diff --git a/target/debian-bookworm-11/lein/Dockerfile b/target/debian-bookworm-11/lein/Dockerfile
index 85b41a59..8b759496 100644
--- a/target/debian-bookworm-11/lein/Dockerfile
+++ b/target/debian-bookworm-11/lein/Dockerfile
@@ -6,39 +6,48 @@ ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
 apt-get update && \
-apt-get install -y make gnupg wget && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apt-get purge -y --auto-remove gnupg wget
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove curl gnupg
 
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 CMD ["lein", "repl"]
diff --git a/target/debian-bookworm-21/latest/rlwrap.retry b/target/debian-bookworm-11/lein/rlwrap.retry
similarity index 100%
rename from target/debian-bookworm-21/latest/rlwrap.retry
rename to target/debian-bookworm-11/lein/rlwrap.retry
diff --git a/target/debian-bookworm-11/tools-deps/Dockerfile b/target/debian-bookworm-11/tools-deps/Dockerfile
index e71c4344..b7778269 100644
--- a/target/debian-bookworm-11/tools-deps/Dockerfile
+++ b/target/debian-bookworm-11/tools-deps/Dockerfile
@@ -4,22 +4,46 @@ ENV JAVA_HOME=/opt/java/openjdk
 COPY --from=eclipse-temurin:11 $JAVA_HOME $JAVA_HOME
 ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
+RUN set -eux; \
 apt-get update && \
-apt-get install -y curl make git rlwrap && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
 clojure -e "(clojure-version)" && \
-apt-get purge -y --auto-remove curl
+apt-get purge -y --auto-remove curl gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009
diff --git a/target/debian-bookworm-17/lein/Dockerfile b/target/debian-bookworm-17/lein/Dockerfile
index a1ebdab5..8e122034 100644
--- a/target/debian-bookworm-17/lein/Dockerfile
+++ b/target/debian-bookworm-17/lein/Dockerfile
@@ -6,40 +6,49 @@ ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
 apt-get update && \
-apt-get install -y make gnupg wget && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apt-get purge -y --auto-remove gnupg wget
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
-
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove curl gnupg
+
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 COPY entrypoint /usr/local/bin/entrypoint
 
diff --git a/target/debian-bookworm-17/lein/rlwrap.retry b/target/debian-bookworm-17/lein/rlwrap.retry
new file mode 100755
index 00000000..83cefbfb
--- /dev/null
+++ b/target/debian-bookworm-17/lein/rlwrap.retry
@@ -0,0 +1,30 @@
+#!/bin/sh
+
+# This script works around a Docker bug that prevents rlwrap from starting
+# right when a container is first started. It is intended to replace
+# /usr/bin/rlwrap and also be named rlwrap but earlier in the PATH
+# (e.g. /usr/local/bin).
+
+max_tries=100 # 100 tries is ~1 second
+try=0
+
+while true; do
+  # see if rlwrap can start at all
+  output=$(/usr/bin/rlwrap true 2>&1 >/dev/null)
+  exit_code=$?
+  if [ $exit_code -gt 0 ]; then
+    # it didn't start
+    try=$((try+1))
+    if [ $try -gt $max_tries ]; then
+      # we're at max attempts so output the error and exit w/ the same code
+      echo "$output" >&2
+      exit $exit_code
+    else
+      # wait a bit and try again
+      sleep 0.01
+    fi
+  else
+    # rlwrap can start so let's run it for real
+    exec /usr/bin/rlwrap "$@"
+  fi
+done
diff --git a/target/debian-bookworm-17/tools-deps/Dockerfile b/target/debian-bookworm-17/tools-deps/Dockerfile
index 9d44578d..4a115f16 100644
--- a/target/debian-bookworm-17/tools-deps/Dockerfile
+++ b/target/debian-bookworm-17/tools-deps/Dockerfile
@@ -4,22 +4,46 @@ ENV JAVA_HOME=/opt/java/openjdk
 COPY --from=eclipse-temurin:17 $JAVA_HOME $JAVA_HOME
 ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
+RUN set -eux; \
 apt-get update && \
-apt-get install -y curl make git rlwrap && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
 clojure -e "(clojure-version)" && \
-apt-get purge -y --auto-remove curl
+apt-get purge -y --auto-remove curl gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009
diff --git a/target/debian-bookworm-21/latest/Dockerfile b/target/debian-bookworm-21/latest/Dockerfile
deleted file mode 100644
index d064f973..00000000
--- a/target/debian-bookworm-21/latest/Dockerfile
+++ /dev/null
@@ -1,73 +0,0 @@
-FROM debian:bookworm
-
-ENV JAVA_HOME=/opt/java/openjdk
-COPY --from=eclipse-temurin:21 $JAVA_HOME $JAVA_HOME
-ENV PATH="${JAVA_HOME}/bin:${PATH}"
-
-
-### INSTALL LEIN ###
-ENV LEIN_VERSION=2.11.2
-ENV LEIN_INSTALL=/usr/local/bin/
-
-WORKDIR /tmp
-
-# Download the whole repo as an archive
-RUN set -eux; \
-apt-get update && \
-apt-get install -y make gnupg wget && \
-rm -rf /var/lib/apt/lists/* && \
-mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
-echo "Comparing lein-pkg checksum ..." && \
-sha256sum lein-pkg && \
-echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
-mv lein-pkg $LEIN_INSTALL/lein && \
-chmod 0755 $LEIN_INSTALL/lein && \
-export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
-gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apt-get purge -y --auto-remove gnupg wget
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
-
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
-
-### INSTALL TOOLS-DEPS ###
-ENV CLOJURE_VERSION=1.11.1.1435
-
-WORKDIR /tmp
-
-RUN \
-apt-get update && \
-apt-get install -y curl make git rlwrap && \
-rm -rf /var/lib/apt/lists/* && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
-clojure -e "(clojure-version)" && \
-apt-get purge -y --auto-remove curl
-
-# Docker bug makes rlwrap crash w/o short sleep first
-# Bug: https://github.com/moby/moby/issues/28009
-# As of 2021-09-10 this bug still exists, despite that issue being closed
-COPY rlwrap.retry /usr/local/bin/rlwrap
-
-COPY entrypoint /usr/local/bin/entrypoint
-
-ENTRYPOINT ["entrypoint"]
-
-CMD ["-M", "--repl"]
diff --git a/target/debian-bookworm-21/latest/entrypoint b/target/debian-bookworm-21/latest/entrypoint
deleted file mode 100755
index 51561d1d..00000000
--- a/target/debian-bookworm-21/latest/entrypoint
+++ /dev/null
@@ -1,21 +0,0 @@
-#!/usr/bin/env bash
-
-set -eou pipefail
-
-entrypoint=clj
-
-cmd=${1:-}
-
-# check if the first arg starts with a hyphen
-if [ "$#" -eq 0 ] || [ "${1#-}" != "$1" ]; then
-  exec "${entrypoint}" "$@"
-fi
-
-if [[ -n "${cmd}" ]]; then
-  # see if help for the subcommand is successful
-  if "${entrypoint}" "${cmd}" --help >/dev/null 2>&1; then
-    exec "${entrypoint}" "$@"
-  fi
-fi
-
-exec "$@"
diff --git a/target/debian-bookworm-21/lein/Dockerfile b/target/debian-bookworm-21/lein/Dockerfile
index 9a1e5071..417a10de 100644
--- a/target/debian-bookworm-21/lein/Dockerfile
+++ b/target/debian-bookworm-21/lein/Dockerfile
@@ -6,40 +6,49 @@ ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
 apt-get update && \
-apt-get install -y make gnupg wget && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apt-get purge -y --auto-remove gnupg wget
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
-
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove curl gnupg
+
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 COPY entrypoint /usr/local/bin/entrypoint
 
diff --git a/target/debian-bookworm-21/lein/rlwrap.retry b/target/debian-bookworm-21/lein/rlwrap.retry
new file mode 100755
index 00000000..83cefbfb
--- /dev/null
+++ b/target/debian-bookworm-21/lein/rlwrap.retry
@@ -0,0 +1,30 @@
+#!/bin/sh
+
+# This script works around a Docker bug that prevents rlwrap from starting
+# right when a container is first started. It is intended to replace
+# /usr/bin/rlwrap and also be named rlwrap but earlier in the PATH
+# (e.g. /usr/local/bin).
+
+max_tries=100 # 100 tries is ~1 second
+try=0
+
+while true; do
+  # see if rlwrap can start at all
+  output=$(/usr/bin/rlwrap true 2>&1 >/dev/null)
+  exit_code=$?
+  if [ $exit_code -gt 0 ]; then
+    # it didn't start
+    try=$((try+1))
+    if [ $try -gt $max_tries ]; then
+      # we're at max attempts so output the error and exit w/ the same code
+      echo "$output" >&2
+      exit $exit_code
+    else
+      # wait a bit and try again
+      sleep 0.01
+    fi
+  else
+    # rlwrap can start so let's run it for real
+    exec /usr/bin/rlwrap "$@"
+  fi
+done
diff --git a/target/debian-bookworm-21/tools-deps/Dockerfile b/target/debian-bookworm-21/tools-deps/Dockerfile
index 90220295..e0c6572c 100644
--- a/target/debian-bookworm-21/tools-deps/Dockerfile
+++ b/target/debian-bookworm-21/tools-deps/Dockerfile
@@ -4,22 +4,46 @@ ENV JAVA_HOME=/opt/java/openjdk
 COPY --from=eclipse-temurin:21 $JAVA_HOME $JAVA_HOME
 ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
+RUN set -eux; \
 apt-get update && \
-apt-get install -y curl make git rlwrap && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
 clojure -e "(clojure-version)" && \
-apt-get purge -y --auto-remove curl
+apt-get purge -y --auto-remove curl gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009
diff --git a/target/debian-bookworm-22/lein/Dockerfile b/target/debian-bookworm-22/lein/Dockerfile
index 954795b9..e4e5d175 100644
--- a/target/debian-bookworm-22/lein/Dockerfile
+++ b/target/debian-bookworm-22/lein/Dockerfile
@@ -6,40 +6,49 @@ ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
 apt-get update && \
-apt-get install -y make gnupg wget && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apt-get purge -y --auto-remove gnupg wget
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
-
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove curl gnupg
+
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 COPY entrypoint /usr/local/bin/entrypoint
 
diff --git a/target/debian-bookworm-22/lein/rlwrap.retry b/target/debian-bookworm-22/lein/rlwrap.retry
new file mode 100755
index 00000000..83cefbfb
--- /dev/null
+++ b/target/debian-bookworm-22/lein/rlwrap.retry
@@ -0,0 +1,30 @@
+#!/bin/sh
+
+# This script works around a Docker bug that prevents rlwrap from starting
+# right when a container is first started. It is intended to replace
+# /usr/bin/rlwrap and also be named rlwrap but earlier in the PATH
+# (e.g. /usr/local/bin).
+
+max_tries=100 # 100 tries is ~1 second
+try=0
+
+while true; do
+  # see if rlwrap can start at all
+  output=$(/usr/bin/rlwrap true 2>&1 >/dev/null)
+  exit_code=$?
+  if [ $exit_code -gt 0 ]; then
+    # it didn't start
+    try=$((try+1))
+    if [ $try -gt $max_tries ]; then
+      # we're at max attempts so output the error and exit w/ the same code
+      echo "$output" >&2
+      exit $exit_code
+    else
+      # wait a bit and try again
+      sleep 0.01
+    fi
+  else
+    # rlwrap can start so let's run it for real
+    exec /usr/bin/rlwrap "$@"
+  fi
+done
diff --git a/target/debian-bookworm-22/tools-deps/Dockerfile b/target/debian-bookworm-22/tools-deps/Dockerfile
index b6f506f2..ca889ebb 100644
--- a/target/debian-bookworm-22/tools-deps/Dockerfile
+++ b/target/debian-bookworm-22/tools-deps/Dockerfile
@@ -4,22 +4,46 @@ ENV JAVA_HOME=/opt/java/openjdk
 COPY --from=eclipse-temurin:22 $JAVA_HOME $JAVA_HOME
 ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
+RUN set -eux; \
 apt-get update && \
-apt-get install -y curl make git rlwrap && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
 clojure -e "(clojure-version)" && \
-apt-get purge -y --auto-remove curl
+apt-get purge -y --auto-remove curl gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009
diff --git a/target/debian-bookworm-8/lein/Dockerfile b/target/debian-bookworm-8/lein/Dockerfile
index da37f93b..d6ef647c 100644
--- a/target/debian-bookworm-8/lein/Dockerfile
+++ b/target/debian-bookworm-8/lein/Dockerfile
@@ -6,39 +6,48 @@ ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
 apt-get update && \
-apt-get install -y make gnupg wget && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apt-get purge -y --auto-remove gnupg wget
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove curl gnupg
 
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 CMD ["lein", "repl"]
diff --git a/target/debian-bookworm-8/lein/rlwrap.retry b/target/debian-bookworm-8/lein/rlwrap.retry
new file mode 100755
index 00000000..83cefbfb
--- /dev/null
+++ b/target/debian-bookworm-8/lein/rlwrap.retry
@@ -0,0 +1,30 @@
+#!/bin/sh
+
+# This script works around a Docker bug that prevents rlwrap from starting
+# right when a container is first started. It is intended to replace
+# /usr/bin/rlwrap and also be named rlwrap but earlier in the PATH
+# (e.g. /usr/local/bin).
+
+max_tries=100 # 100 tries is ~1 second
+try=0
+
+while true; do
+  # see if rlwrap can start at all
+  output=$(/usr/bin/rlwrap true 2>&1 >/dev/null)
+  exit_code=$?
+  if [ $exit_code -gt 0 ]; then
+    # it didn't start
+    try=$((try+1))
+    if [ $try -gt $max_tries ]; then
+      # we're at max attempts so output the error and exit w/ the same code
+      echo "$output" >&2
+      exit $exit_code
+    else
+      # wait a bit and try again
+      sleep 0.01
+    fi
+  else
+    # rlwrap can start so let's run it for real
+    exec /usr/bin/rlwrap "$@"
+  fi
+done
diff --git a/target/debian-bookworm-8/tools-deps/Dockerfile b/target/debian-bookworm-8/tools-deps/Dockerfile
index 777ee3b7..63181fa0 100644
--- a/target/debian-bookworm-8/tools-deps/Dockerfile
+++ b/target/debian-bookworm-8/tools-deps/Dockerfile
@@ -4,22 +4,46 @@ ENV JAVA_HOME=/opt/java/openjdk
 COPY --from=eclipse-temurin:8 $JAVA_HOME $JAVA_HOME
 ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
+RUN set -eux; \
 apt-get update && \
-apt-get install -y curl make git rlwrap && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
 clojure -e "(clojure-version)" && \
-apt-get purge -y --auto-remove curl
+apt-get purge -y --auto-remove curl gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009
diff --git a/target/debian-bookworm-slim-11/lein/Dockerfile b/target/debian-bookworm-slim-11/lein/Dockerfile
index 82cb00a9..f0afd713 100644
--- a/target/debian-bookworm-slim-11/lein/Dockerfile
+++ b/target/debian-bookworm-slim-11/lein/Dockerfile
@@ -6,39 +6,48 @@ ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
 apt-get update && \
-apt-get install -y gnupg wget && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apt-get purge -y --auto-remove gnupg wget
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove curl gnupg
 
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 CMD ["lein", "repl"]
diff --git a/target/debian-bookworm-slim-11/lein/rlwrap.retry b/target/debian-bookworm-slim-11/lein/rlwrap.retry
new file mode 100755
index 00000000..83cefbfb
--- /dev/null
+++ b/target/debian-bookworm-slim-11/lein/rlwrap.retry
@@ -0,0 +1,30 @@
+#!/bin/sh
+
+# This script works around a Docker bug that prevents rlwrap from starting
+# right when a container is first started. It is intended to replace
+# /usr/bin/rlwrap and also be named rlwrap but earlier in the PATH
+# (e.g. /usr/local/bin).
+
+max_tries=100 # 100 tries is ~1 second
+try=0
+
+while true; do
+  # see if rlwrap can start at all
+  output=$(/usr/bin/rlwrap true 2>&1 >/dev/null)
+  exit_code=$?
+  if [ $exit_code -gt 0 ]; then
+    # it didn't start
+    try=$((try+1))
+    if [ $try -gt $max_tries ]; then
+      # we're at max attempts so output the error and exit w/ the same code
+      echo "$output" >&2
+      exit $exit_code
+    else
+      # wait a bit and try again
+      sleep 0.01
+    fi
+  else
+    # rlwrap can start so let's run it for real
+    exec /usr/bin/rlwrap "$@"
+  fi
+done
diff --git a/target/debian-bookworm-slim-11/tools-deps/Dockerfile b/target/debian-bookworm-slim-11/tools-deps/Dockerfile
index 5f8c741d..2d3a8d22 100644
--- a/target/debian-bookworm-slim-11/tools-deps/Dockerfile
+++ b/target/debian-bookworm-slim-11/tools-deps/Dockerfile
@@ -4,22 +4,46 @@ ENV JAVA_HOME=/opt/java/openjdk
 COPY --from=eclipse-temurin:11 $JAVA_HOME $JAVA_HOME
 ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
+RUN set -eux; \
 apt-get update && \
-apt-get install -y curl make git rlwrap && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
 clojure -e "(clojure-version)" && \
-apt-get purge -y --auto-remove curl
+apt-get purge -y --auto-remove curl gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009
diff --git a/target/debian-bookworm-slim-17/lein/Dockerfile b/target/debian-bookworm-slim-17/lein/Dockerfile
index 99fd72c5..3d79f9e2 100644
--- a/target/debian-bookworm-slim-17/lein/Dockerfile
+++ b/target/debian-bookworm-slim-17/lein/Dockerfile
@@ -6,40 +6,49 @@ ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
 apt-get update && \
-apt-get install -y gnupg wget && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apt-get purge -y --auto-remove gnupg wget
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
-
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove curl gnupg
+
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 COPY entrypoint /usr/local/bin/entrypoint
 
diff --git a/target/debian-bookworm-slim-17/lein/rlwrap.retry b/target/debian-bookworm-slim-17/lein/rlwrap.retry
new file mode 100755
index 00000000..83cefbfb
--- /dev/null
+++ b/target/debian-bookworm-slim-17/lein/rlwrap.retry
@@ -0,0 +1,30 @@
+#!/bin/sh
+
+# This script works around a Docker bug that prevents rlwrap from starting
+# right when a container is first started. It is intended to replace
+# /usr/bin/rlwrap and also be named rlwrap but earlier in the PATH
+# (e.g. /usr/local/bin).
+
+max_tries=100 # 100 tries is ~1 second
+try=0
+
+while true; do
+  # see if rlwrap can start at all
+  output=$(/usr/bin/rlwrap true 2>&1 >/dev/null)
+  exit_code=$?
+  if [ $exit_code -gt 0 ]; then
+    # it didn't start
+    try=$((try+1))
+    if [ $try -gt $max_tries ]; then
+      # we're at max attempts so output the error and exit w/ the same code
+      echo "$output" >&2
+      exit $exit_code
+    else
+      # wait a bit and try again
+      sleep 0.01
+    fi
+  else
+    # rlwrap can start so let's run it for real
+    exec /usr/bin/rlwrap "$@"
+  fi
+done
diff --git a/target/debian-bookworm-slim-17/tools-deps/Dockerfile b/target/debian-bookworm-slim-17/tools-deps/Dockerfile
index 4aad2597..a9e3a64b 100644
--- a/target/debian-bookworm-slim-17/tools-deps/Dockerfile
+++ b/target/debian-bookworm-slim-17/tools-deps/Dockerfile
@@ -4,22 +4,46 @@ ENV JAVA_HOME=/opt/java/openjdk
 COPY --from=eclipse-temurin:17 $JAVA_HOME $JAVA_HOME
 ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
+RUN set -eux; \
 apt-get update && \
-apt-get install -y curl make git rlwrap && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
 clojure -e "(clojure-version)" && \
-apt-get purge -y --auto-remove curl
+apt-get purge -y --auto-remove curl gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009
diff --git a/target/debian-bookworm-slim-21/lein/Dockerfile b/target/debian-bookworm-slim-21/lein/Dockerfile
index 1b8d9820..2fd1a1e6 100644
--- a/target/debian-bookworm-slim-21/lein/Dockerfile
+++ b/target/debian-bookworm-slim-21/lein/Dockerfile
@@ -6,40 +6,49 @@ ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
 apt-get update && \
-apt-get install -y gnupg wget && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apt-get purge -y --auto-remove gnupg wget
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
-
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove curl gnupg
+
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 COPY entrypoint /usr/local/bin/entrypoint
 
diff --git a/target/debian-bookworm-slim-21/lein/rlwrap.retry b/target/debian-bookworm-slim-21/lein/rlwrap.retry
new file mode 100755
index 00000000..83cefbfb
--- /dev/null
+++ b/target/debian-bookworm-slim-21/lein/rlwrap.retry
@@ -0,0 +1,30 @@
+#!/bin/sh
+
+# This script works around a Docker bug that prevents rlwrap from starting
+# right when a container is first started. It is intended to replace
+# /usr/bin/rlwrap and also be named rlwrap but earlier in the PATH
+# (e.g. /usr/local/bin).
+
+max_tries=100 # 100 tries is ~1 second
+try=0
+
+while true; do
+  # see if rlwrap can start at all
+  output=$(/usr/bin/rlwrap true 2>&1 >/dev/null)
+  exit_code=$?
+  if [ $exit_code -gt 0 ]; then
+    # it didn't start
+    try=$((try+1))
+    if [ $try -gt $max_tries ]; then
+      # we're at max attempts so output the error and exit w/ the same code
+      echo "$output" >&2
+      exit $exit_code
+    else
+      # wait a bit and try again
+      sleep 0.01
+    fi
+  else
+    # rlwrap can start so let's run it for real
+    exec /usr/bin/rlwrap "$@"
+  fi
+done
diff --git a/target/debian-bookworm-slim-21/tools-deps/Dockerfile b/target/debian-bookworm-slim-21/tools-deps/Dockerfile
index d88192a6..2ee0ec0a 100644
--- a/target/debian-bookworm-slim-21/tools-deps/Dockerfile
+++ b/target/debian-bookworm-slim-21/tools-deps/Dockerfile
@@ -4,22 +4,46 @@ ENV JAVA_HOME=/opt/java/openjdk
 COPY --from=eclipse-temurin:21 $JAVA_HOME $JAVA_HOME
 ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
+RUN set -eux; \
 apt-get update && \
-apt-get install -y curl make git rlwrap && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
 clojure -e "(clojure-version)" && \
-apt-get purge -y --auto-remove curl
+apt-get purge -y --auto-remove curl gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009
diff --git a/target/debian-bookworm-slim-22/lein/Dockerfile b/target/debian-bookworm-slim-22/lein/Dockerfile
index 054c0dfc..f60c74dd 100644
--- a/target/debian-bookworm-slim-22/lein/Dockerfile
+++ b/target/debian-bookworm-slim-22/lein/Dockerfile
@@ -6,40 +6,49 @@ ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
 apt-get update && \
-apt-get install -y gnupg wget && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apt-get purge -y --auto-remove gnupg wget
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
-
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove curl gnupg
+
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 COPY entrypoint /usr/local/bin/entrypoint
 
diff --git a/target/debian-bookworm-slim-22/lein/rlwrap.retry b/target/debian-bookworm-slim-22/lein/rlwrap.retry
new file mode 100755
index 00000000..83cefbfb
--- /dev/null
+++ b/target/debian-bookworm-slim-22/lein/rlwrap.retry
@@ -0,0 +1,30 @@
+#!/bin/sh
+
+# This script works around a Docker bug that prevents rlwrap from starting
+# right when a container is first started. It is intended to replace
+# /usr/bin/rlwrap and also be named rlwrap but earlier in the PATH
+# (e.g. /usr/local/bin).
+
+max_tries=100 # 100 tries is ~1 second
+try=0
+
+while true; do
+  # see if rlwrap can start at all
+  output=$(/usr/bin/rlwrap true 2>&1 >/dev/null)
+  exit_code=$?
+  if [ $exit_code -gt 0 ]; then
+    # it didn't start
+    try=$((try+1))
+    if [ $try -gt $max_tries ]; then
+      # we're at max attempts so output the error and exit w/ the same code
+      echo "$output" >&2
+      exit $exit_code
+    else
+      # wait a bit and try again
+      sleep 0.01
+    fi
+  else
+    # rlwrap can start so let's run it for real
+    exec /usr/bin/rlwrap "$@"
+  fi
+done
diff --git a/target/debian-bookworm-slim-22/tools-deps/Dockerfile b/target/debian-bookworm-slim-22/tools-deps/Dockerfile
index 9ad2cd59..0ac32592 100644
--- a/target/debian-bookworm-slim-22/tools-deps/Dockerfile
+++ b/target/debian-bookworm-slim-22/tools-deps/Dockerfile
@@ -4,22 +4,46 @@ ENV JAVA_HOME=/opt/java/openjdk
 COPY --from=eclipse-temurin:22 $JAVA_HOME $JAVA_HOME
 ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
+RUN set -eux; \
 apt-get update && \
-apt-get install -y curl make git rlwrap && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
 clojure -e "(clojure-version)" && \
-apt-get purge -y --auto-remove curl
+apt-get purge -y --auto-remove curl gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009
diff --git a/target/debian-bookworm-slim-8/lein/Dockerfile b/target/debian-bookworm-slim-8/lein/Dockerfile
index 1d5f9697..6e3c619f 100644
--- a/target/debian-bookworm-slim-8/lein/Dockerfile
+++ b/target/debian-bookworm-slim-8/lein/Dockerfile
@@ -6,39 +6,48 @@ ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
 apt-get update && \
-apt-get install -y gnupg wget && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apt-get purge -y --auto-remove gnupg wget
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove curl gnupg
 
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 CMD ["lein", "repl"]
diff --git a/target/debian-bookworm-slim-8/lein/rlwrap.retry b/target/debian-bookworm-slim-8/lein/rlwrap.retry
new file mode 100755
index 00000000..83cefbfb
--- /dev/null
+++ b/target/debian-bookworm-slim-8/lein/rlwrap.retry
@@ -0,0 +1,30 @@
+#!/bin/sh
+
+# This script works around a Docker bug that prevents rlwrap from starting
+# right when a container is first started. It is intended to replace
+# /usr/bin/rlwrap and also be named rlwrap but earlier in the PATH
+# (e.g. /usr/local/bin).
+
+max_tries=100 # 100 tries is ~1 second
+try=0
+
+while true; do
+  # see if rlwrap can start at all
+  output=$(/usr/bin/rlwrap true 2>&1 >/dev/null)
+  exit_code=$?
+  if [ $exit_code -gt 0 ]; then
+    # it didn't start
+    try=$((try+1))
+    if [ $try -gt $max_tries ]; then
+      # we're at max attempts so output the error and exit w/ the same code
+      echo "$output" >&2
+      exit $exit_code
+    else
+      # wait a bit and try again
+      sleep 0.01
+    fi
+  else
+    # rlwrap can start so let's run it for real
+    exec /usr/bin/rlwrap "$@"
+  fi
+done
diff --git a/target/debian-bookworm-slim-8/tools-deps/Dockerfile b/target/debian-bookworm-slim-8/tools-deps/Dockerfile
index 12164e98..bd843a34 100644
--- a/target/debian-bookworm-slim-8/tools-deps/Dockerfile
+++ b/target/debian-bookworm-slim-8/tools-deps/Dockerfile
@@ -4,22 +4,46 @@ ENV JAVA_HOME=/opt/java/openjdk
 COPY --from=eclipse-temurin:8 $JAVA_HOME $JAVA_HOME
 ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
+RUN set -eux; \
 apt-get update && \
-apt-get install -y curl make git rlwrap && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
 clojure -e "(clojure-version)" && \
-apt-get purge -y --auto-remove curl
+apt-get purge -y --auto-remove curl gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009
diff --git a/target/debian-bullseye-11/lein/Dockerfile b/target/debian-bullseye-11/lein/Dockerfile
index 6e7ad388..89198e13 100644
--- a/target/debian-bullseye-11/lein/Dockerfile
+++ b/target/debian-bullseye-11/lein/Dockerfile
@@ -6,39 +6,48 @@ ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
 apt-get update && \
-apt-get install -y make gnupg wget && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apt-get purge -y --auto-remove gnupg wget
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove curl gnupg
 
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 CMD ["lein", "repl"]
diff --git a/target/debian-bullseye-11/lein/rlwrap.retry b/target/debian-bullseye-11/lein/rlwrap.retry
new file mode 100755
index 00000000..83cefbfb
--- /dev/null
+++ b/target/debian-bullseye-11/lein/rlwrap.retry
@@ -0,0 +1,30 @@
+#!/bin/sh
+
+# This script works around a Docker bug that prevents rlwrap from starting
+# right when a container is first started. It is intended to replace
+# /usr/bin/rlwrap and also be named rlwrap but earlier in the PATH
+# (e.g. /usr/local/bin).
+
+max_tries=100 # 100 tries is ~1 second
+try=0
+
+while true; do
+  # see if rlwrap can start at all
+  output=$(/usr/bin/rlwrap true 2>&1 >/dev/null)
+  exit_code=$?
+  if [ $exit_code -gt 0 ]; then
+    # it didn't start
+    try=$((try+1))
+    if [ $try -gt $max_tries ]; then
+      # we're at max attempts so output the error and exit w/ the same code
+      echo "$output" >&2
+      exit $exit_code
+    else
+      # wait a bit and try again
+      sleep 0.01
+    fi
+  else
+    # rlwrap can start so let's run it for real
+    exec /usr/bin/rlwrap "$@"
+  fi
+done
diff --git a/target/debian-bullseye-11/tools-deps/Dockerfile b/target/debian-bullseye-11/tools-deps/Dockerfile
index 6b5a1e1e..e0518306 100644
--- a/target/debian-bullseye-11/tools-deps/Dockerfile
+++ b/target/debian-bullseye-11/tools-deps/Dockerfile
@@ -4,22 +4,46 @@ ENV JAVA_HOME=/opt/java/openjdk
 COPY --from=eclipse-temurin:11 $JAVA_HOME $JAVA_HOME
 ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
+RUN set -eux; \
 apt-get update && \
-apt-get install -y curl make git rlwrap && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
 clojure -e "(clojure-version)" && \
-apt-get purge -y --auto-remove curl
+apt-get purge -y --auto-remove curl gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009
diff --git a/target/debian-bullseye-17/lein/Dockerfile b/target/debian-bullseye-17/lein/Dockerfile
index 5b51e29f..99dc5678 100644
--- a/target/debian-bullseye-17/lein/Dockerfile
+++ b/target/debian-bullseye-17/lein/Dockerfile
@@ -6,40 +6,49 @@ ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
 apt-get update && \
-apt-get install -y make gnupg wget && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apt-get purge -y --auto-remove gnupg wget
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
-
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove curl gnupg
+
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 COPY entrypoint /usr/local/bin/entrypoint
 
diff --git a/target/debian-bullseye-17/lein/rlwrap.retry b/target/debian-bullseye-17/lein/rlwrap.retry
new file mode 100755
index 00000000..83cefbfb
--- /dev/null
+++ b/target/debian-bullseye-17/lein/rlwrap.retry
@@ -0,0 +1,30 @@
+#!/bin/sh
+
+# This script works around a Docker bug that prevents rlwrap from starting
+# right when a container is first started. It is intended to replace
+# /usr/bin/rlwrap and also be named rlwrap but earlier in the PATH
+# (e.g. /usr/local/bin).
+
+max_tries=100 # 100 tries is ~1 second
+try=0
+
+while true; do
+  # see if rlwrap can start at all
+  output=$(/usr/bin/rlwrap true 2>&1 >/dev/null)
+  exit_code=$?
+  if [ $exit_code -gt 0 ]; then
+    # it didn't start
+    try=$((try+1))
+    if [ $try -gt $max_tries ]; then
+      # we're at max attempts so output the error and exit w/ the same code
+      echo "$output" >&2
+      exit $exit_code
+    else
+      # wait a bit and try again
+      sleep 0.01
+    fi
+  else
+    # rlwrap can start so let's run it for real
+    exec /usr/bin/rlwrap "$@"
+  fi
+done
diff --git a/target/debian-bullseye-17/tools-deps/Dockerfile b/target/debian-bullseye-17/tools-deps/Dockerfile
index 176b2792..88f76a12 100644
--- a/target/debian-bullseye-17/tools-deps/Dockerfile
+++ b/target/debian-bullseye-17/tools-deps/Dockerfile
@@ -4,22 +4,46 @@ ENV JAVA_HOME=/opt/java/openjdk
 COPY --from=eclipse-temurin:17 $JAVA_HOME $JAVA_HOME
 ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
+RUN set -eux; \
 apt-get update && \
-apt-get install -y curl make git rlwrap && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
 clojure -e "(clojure-version)" && \
-apt-get purge -y --auto-remove curl
+apt-get purge -y --auto-remove curl gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009
diff --git a/target/debian-bullseye-21/lein/Dockerfile b/target/debian-bullseye-21/lein/Dockerfile
index aa335e9e..3e1b3bef 100644
--- a/target/debian-bullseye-21/lein/Dockerfile
+++ b/target/debian-bullseye-21/lein/Dockerfile
@@ -6,40 +6,49 @@ ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
 apt-get update && \
-apt-get install -y make gnupg wget && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apt-get purge -y --auto-remove gnupg wget
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
-
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove curl gnupg
+
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 COPY entrypoint /usr/local/bin/entrypoint
 
diff --git a/target/debian-bullseye-21/lein/rlwrap.retry b/target/debian-bullseye-21/lein/rlwrap.retry
new file mode 100755
index 00000000..83cefbfb
--- /dev/null
+++ b/target/debian-bullseye-21/lein/rlwrap.retry
@@ -0,0 +1,30 @@
+#!/bin/sh
+
+# This script works around a Docker bug that prevents rlwrap from starting
+# right when a container is first started. It is intended to replace
+# /usr/bin/rlwrap and also be named rlwrap but earlier in the PATH
+# (e.g. /usr/local/bin).
+
+max_tries=100 # 100 tries is ~1 second
+try=0
+
+while true; do
+  # see if rlwrap can start at all
+  output=$(/usr/bin/rlwrap true 2>&1 >/dev/null)
+  exit_code=$?
+  if [ $exit_code -gt 0 ]; then
+    # it didn't start
+    try=$((try+1))
+    if [ $try -gt $max_tries ]; then
+      # we're at max attempts so output the error and exit w/ the same code
+      echo "$output" >&2
+      exit $exit_code
+    else
+      # wait a bit and try again
+      sleep 0.01
+    fi
+  else
+    # rlwrap can start so let's run it for real
+    exec /usr/bin/rlwrap "$@"
+  fi
+done
diff --git a/target/debian-bullseye-21/tools-deps/Dockerfile b/target/debian-bullseye-21/tools-deps/Dockerfile
index 9326e92d..148159fa 100644
--- a/target/debian-bullseye-21/tools-deps/Dockerfile
+++ b/target/debian-bullseye-21/tools-deps/Dockerfile
@@ -4,22 +4,46 @@ ENV JAVA_HOME=/opt/java/openjdk
 COPY --from=eclipse-temurin:21 $JAVA_HOME $JAVA_HOME
 ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
+RUN set -eux; \
 apt-get update && \
-apt-get install -y curl make git rlwrap && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
 clojure -e "(clojure-version)" && \
-apt-get purge -y --auto-remove curl
+apt-get purge -y --auto-remove curl gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009
diff --git a/target/debian-bullseye-22/lein/Dockerfile b/target/debian-bullseye-22/lein/Dockerfile
index 46ebc8f5..d1ebede4 100644
--- a/target/debian-bullseye-22/lein/Dockerfile
+++ b/target/debian-bullseye-22/lein/Dockerfile
@@ -6,40 +6,49 @@ ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
 apt-get update && \
-apt-get install -y make gnupg wget && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apt-get purge -y --auto-remove gnupg wget
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
-
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove curl gnupg
+
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 COPY entrypoint /usr/local/bin/entrypoint
 
diff --git a/target/debian-bullseye-22/lein/rlwrap.retry b/target/debian-bullseye-22/lein/rlwrap.retry
new file mode 100755
index 00000000..83cefbfb
--- /dev/null
+++ b/target/debian-bullseye-22/lein/rlwrap.retry
@@ -0,0 +1,30 @@
+#!/bin/sh
+
+# This script works around a Docker bug that prevents rlwrap from starting
+# right when a container is first started. It is intended to replace
+# /usr/bin/rlwrap and also be named rlwrap but earlier in the PATH
+# (e.g. /usr/local/bin).
+
+max_tries=100 # 100 tries is ~1 second
+try=0
+
+while true; do
+  # see if rlwrap can start at all
+  output=$(/usr/bin/rlwrap true 2>&1 >/dev/null)
+  exit_code=$?
+  if [ $exit_code -gt 0 ]; then
+    # it didn't start
+    try=$((try+1))
+    if [ $try -gt $max_tries ]; then
+      # we're at max attempts so output the error and exit w/ the same code
+      echo "$output" >&2
+      exit $exit_code
+    else
+      # wait a bit and try again
+      sleep 0.01
+    fi
+  else
+    # rlwrap can start so let's run it for real
+    exec /usr/bin/rlwrap "$@"
+  fi
+done
diff --git a/target/debian-bullseye-22/tools-deps/Dockerfile b/target/debian-bullseye-22/tools-deps/Dockerfile
index 97fcd812..e21cce3d 100644
--- a/target/debian-bullseye-22/tools-deps/Dockerfile
+++ b/target/debian-bullseye-22/tools-deps/Dockerfile
@@ -4,22 +4,46 @@ ENV JAVA_HOME=/opt/java/openjdk
 COPY --from=eclipse-temurin:22 $JAVA_HOME $JAVA_HOME
 ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
+RUN set -eux; \
 apt-get update && \
-apt-get install -y curl make git rlwrap && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
 clojure -e "(clojure-version)" && \
-apt-get purge -y --auto-remove curl
+apt-get purge -y --auto-remove curl gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009
diff --git a/target/debian-bullseye-8/lein/Dockerfile b/target/debian-bullseye-8/lein/Dockerfile
index 72e9a4a2..adccfa89 100644
--- a/target/debian-bullseye-8/lein/Dockerfile
+++ b/target/debian-bullseye-8/lein/Dockerfile
@@ -6,39 +6,48 @@ ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
 apt-get update && \
-apt-get install -y make gnupg wget && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apt-get purge -y --auto-remove gnupg wget
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove curl gnupg
 
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 CMD ["lein", "repl"]
diff --git a/target/debian-bullseye-8/lein/rlwrap.retry b/target/debian-bullseye-8/lein/rlwrap.retry
new file mode 100755
index 00000000..83cefbfb
--- /dev/null
+++ b/target/debian-bullseye-8/lein/rlwrap.retry
@@ -0,0 +1,30 @@
+#!/bin/sh
+
+# This script works around a Docker bug that prevents rlwrap from starting
+# right when a container is first started. It is intended to replace
+# /usr/bin/rlwrap and also be named rlwrap but earlier in the PATH
+# (e.g. /usr/local/bin).
+
+max_tries=100 # 100 tries is ~1 second
+try=0
+
+while true; do
+  # see if rlwrap can start at all
+  output=$(/usr/bin/rlwrap true 2>&1 >/dev/null)
+  exit_code=$?
+  if [ $exit_code -gt 0 ]; then
+    # it didn't start
+    try=$((try+1))
+    if [ $try -gt $max_tries ]; then
+      # we're at max attempts so output the error and exit w/ the same code
+      echo "$output" >&2
+      exit $exit_code
+    else
+      # wait a bit and try again
+      sleep 0.01
+    fi
+  else
+    # rlwrap can start so let's run it for real
+    exec /usr/bin/rlwrap "$@"
+  fi
+done
diff --git a/target/debian-bullseye-8/tools-deps/Dockerfile b/target/debian-bullseye-8/tools-deps/Dockerfile
index 4daee8f9..f070d90c 100644
--- a/target/debian-bullseye-8/tools-deps/Dockerfile
+++ b/target/debian-bullseye-8/tools-deps/Dockerfile
@@ -4,22 +4,46 @@ ENV JAVA_HOME=/opt/java/openjdk
 COPY --from=eclipse-temurin:8 $JAVA_HOME $JAVA_HOME
 ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
+RUN set -eux; \
 apt-get update && \
-apt-get install -y curl make git rlwrap && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
 clojure -e "(clojure-version)" && \
-apt-get purge -y --auto-remove curl
+apt-get purge -y --auto-remove curl gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009
diff --git a/target/debian-bullseye-slim-11/lein/Dockerfile b/target/debian-bullseye-slim-11/lein/Dockerfile
index aa27e2f9..e9c86de8 100644
--- a/target/debian-bullseye-slim-11/lein/Dockerfile
+++ b/target/debian-bullseye-slim-11/lein/Dockerfile
@@ -6,39 +6,48 @@ ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
 apt-get update && \
-apt-get install -y gnupg wget && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apt-get purge -y --auto-remove gnupg wget
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove curl gnupg
 
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 CMD ["lein", "repl"]
diff --git a/target/debian-bullseye-slim-11/lein/rlwrap.retry b/target/debian-bullseye-slim-11/lein/rlwrap.retry
new file mode 100755
index 00000000..83cefbfb
--- /dev/null
+++ b/target/debian-bullseye-slim-11/lein/rlwrap.retry
@@ -0,0 +1,30 @@
+#!/bin/sh
+
+# This script works around a Docker bug that prevents rlwrap from starting
+# right when a container is first started. It is intended to replace
+# /usr/bin/rlwrap and also be named rlwrap but earlier in the PATH
+# (e.g. /usr/local/bin).
+
+max_tries=100 # 100 tries is ~1 second
+try=0
+
+while true; do
+  # see if rlwrap can start at all
+  output=$(/usr/bin/rlwrap true 2>&1 >/dev/null)
+  exit_code=$?
+  if [ $exit_code -gt 0 ]; then
+    # it didn't start
+    try=$((try+1))
+    if [ $try -gt $max_tries ]; then
+      # we're at max attempts so output the error and exit w/ the same code
+      echo "$output" >&2
+      exit $exit_code
+    else
+      # wait a bit and try again
+      sleep 0.01
+    fi
+  else
+    # rlwrap can start so let's run it for real
+    exec /usr/bin/rlwrap "$@"
+  fi
+done
diff --git a/target/debian-bullseye-slim-11/tools-deps/Dockerfile b/target/debian-bullseye-slim-11/tools-deps/Dockerfile
index 50d94454..e15543a4 100644
--- a/target/debian-bullseye-slim-11/tools-deps/Dockerfile
+++ b/target/debian-bullseye-slim-11/tools-deps/Dockerfile
@@ -4,22 +4,46 @@ ENV JAVA_HOME=/opt/java/openjdk
 COPY --from=eclipse-temurin:11 $JAVA_HOME $JAVA_HOME
 ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
+RUN set -eux; \
 apt-get update && \
-apt-get install -y curl make git rlwrap && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
 clojure -e "(clojure-version)" && \
-apt-get purge -y --auto-remove curl
+apt-get purge -y --auto-remove curl gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009
diff --git a/target/debian-bullseye-slim-17/lein/Dockerfile b/target/debian-bullseye-slim-17/lein/Dockerfile
index ef84cab4..01e722c4 100644
--- a/target/debian-bullseye-slim-17/lein/Dockerfile
+++ b/target/debian-bullseye-slim-17/lein/Dockerfile
@@ -6,40 +6,49 @@ ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
 apt-get update && \
-apt-get install -y gnupg wget && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apt-get purge -y --auto-remove gnupg wget
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
-
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove curl gnupg
+
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 COPY entrypoint /usr/local/bin/entrypoint
 
diff --git a/target/debian-bullseye-slim-17/lein/rlwrap.retry b/target/debian-bullseye-slim-17/lein/rlwrap.retry
new file mode 100755
index 00000000..83cefbfb
--- /dev/null
+++ b/target/debian-bullseye-slim-17/lein/rlwrap.retry
@@ -0,0 +1,30 @@
+#!/bin/sh
+
+# This script works around a Docker bug that prevents rlwrap from starting
+# right when a container is first started. It is intended to replace
+# /usr/bin/rlwrap and also be named rlwrap but earlier in the PATH
+# (e.g. /usr/local/bin).
+
+max_tries=100 # 100 tries is ~1 second
+try=0
+
+while true; do
+  # see if rlwrap can start at all
+  output=$(/usr/bin/rlwrap true 2>&1 >/dev/null)
+  exit_code=$?
+  if [ $exit_code -gt 0 ]; then
+    # it didn't start
+    try=$((try+1))
+    if [ $try -gt $max_tries ]; then
+      # we're at max attempts so output the error and exit w/ the same code
+      echo "$output" >&2
+      exit $exit_code
+    else
+      # wait a bit and try again
+      sleep 0.01
+    fi
+  else
+    # rlwrap can start so let's run it for real
+    exec /usr/bin/rlwrap "$@"
+  fi
+done
diff --git a/target/debian-bullseye-slim-17/tools-deps/Dockerfile b/target/debian-bullseye-slim-17/tools-deps/Dockerfile
index 28dac307..6c2c2754 100644
--- a/target/debian-bullseye-slim-17/tools-deps/Dockerfile
+++ b/target/debian-bullseye-slim-17/tools-deps/Dockerfile
@@ -4,22 +4,46 @@ ENV JAVA_HOME=/opt/java/openjdk
 COPY --from=eclipse-temurin:17 $JAVA_HOME $JAVA_HOME
 ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
+RUN set -eux; \
 apt-get update && \
-apt-get install -y curl make git rlwrap && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
 clojure -e "(clojure-version)" && \
-apt-get purge -y --auto-remove curl
+apt-get purge -y --auto-remove curl gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009
diff --git a/target/debian-bullseye-slim-21/lein/Dockerfile b/target/debian-bullseye-slim-21/lein/Dockerfile
index 37c0e8ff..40d53748 100644
--- a/target/debian-bullseye-slim-21/lein/Dockerfile
+++ b/target/debian-bullseye-slim-21/lein/Dockerfile
@@ -6,40 +6,49 @@ ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
 apt-get update && \
-apt-get install -y gnupg wget && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apt-get purge -y --auto-remove gnupg wget
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
-
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove curl gnupg
+
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 COPY entrypoint /usr/local/bin/entrypoint
 
diff --git a/target/debian-bullseye-slim-21/lein/rlwrap.retry b/target/debian-bullseye-slim-21/lein/rlwrap.retry
new file mode 100755
index 00000000..83cefbfb
--- /dev/null
+++ b/target/debian-bullseye-slim-21/lein/rlwrap.retry
@@ -0,0 +1,30 @@
+#!/bin/sh
+
+# This script works around a Docker bug that prevents rlwrap from starting
+# right when a container is first started. It is intended to replace
+# /usr/bin/rlwrap and also be named rlwrap but earlier in the PATH
+# (e.g. /usr/local/bin).
+
+max_tries=100 # 100 tries is ~1 second
+try=0
+
+while true; do
+  # see if rlwrap can start at all
+  output=$(/usr/bin/rlwrap true 2>&1 >/dev/null)
+  exit_code=$?
+  if [ $exit_code -gt 0 ]; then
+    # it didn't start
+    try=$((try+1))
+    if [ $try -gt $max_tries ]; then
+      # we're at max attempts so output the error and exit w/ the same code
+      echo "$output" >&2
+      exit $exit_code
+    else
+      # wait a bit and try again
+      sleep 0.01
+    fi
+  else
+    # rlwrap can start so let's run it for real
+    exec /usr/bin/rlwrap "$@"
+  fi
+done
diff --git a/target/debian-bullseye-slim-21/tools-deps/Dockerfile b/target/debian-bullseye-slim-21/tools-deps/Dockerfile
index 4412f8c1..0a5c47a5 100644
--- a/target/debian-bullseye-slim-21/tools-deps/Dockerfile
+++ b/target/debian-bullseye-slim-21/tools-deps/Dockerfile
@@ -4,22 +4,46 @@ ENV JAVA_HOME=/opt/java/openjdk
 COPY --from=eclipse-temurin:21 $JAVA_HOME $JAVA_HOME
 ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
+RUN set -eux; \
 apt-get update && \
-apt-get install -y curl make git rlwrap && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
 clojure -e "(clojure-version)" && \
-apt-get purge -y --auto-remove curl
+apt-get purge -y --auto-remove curl gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009
diff --git a/target/debian-bullseye-slim-22/lein/Dockerfile b/target/debian-bullseye-slim-22/lein/Dockerfile
index 86016b83..d2e1fb6a 100644
--- a/target/debian-bullseye-slim-22/lein/Dockerfile
+++ b/target/debian-bullseye-slim-22/lein/Dockerfile
@@ -6,40 +6,49 @@ ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
 apt-get update && \
-apt-get install -y gnupg wget && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apt-get purge -y --auto-remove gnupg wget
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
-
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove curl gnupg
+
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 COPY entrypoint /usr/local/bin/entrypoint
 
diff --git a/target/debian-bullseye-slim-22/lein/rlwrap.retry b/target/debian-bullseye-slim-22/lein/rlwrap.retry
new file mode 100755
index 00000000..83cefbfb
--- /dev/null
+++ b/target/debian-bullseye-slim-22/lein/rlwrap.retry
@@ -0,0 +1,30 @@
+#!/bin/sh
+
+# This script works around a Docker bug that prevents rlwrap from starting
+# right when a container is first started. It is intended to replace
+# /usr/bin/rlwrap and also be named rlwrap but earlier in the PATH
+# (e.g. /usr/local/bin).
+
+max_tries=100 # 100 tries is ~1 second
+try=0
+
+while true; do
+  # see if rlwrap can start at all
+  output=$(/usr/bin/rlwrap true 2>&1 >/dev/null)
+  exit_code=$?
+  if [ $exit_code -gt 0 ]; then
+    # it didn't start
+    try=$((try+1))
+    if [ $try -gt $max_tries ]; then
+      # we're at max attempts so output the error and exit w/ the same code
+      echo "$output" >&2
+      exit $exit_code
+    else
+      # wait a bit and try again
+      sleep 0.01
+    fi
+  else
+    # rlwrap can start so let's run it for real
+    exec /usr/bin/rlwrap "$@"
+  fi
+done
diff --git a/target/debian-bullseye-slim-22/tools-deps/Dockerfile b/target/debian-bullseye-slim-22/tools-deps/Dockerfile
index 895f0d20..94f3ade3 100644
--- a/target/debian-bullseye-slim-22/tools-deps/Dockerfile
+++ b/target/debian-bullseye-slim-22/tools-deps/Dockerfile
@@ -4,22 +4,46 @@ ENV JAVA_HOME=/opt/java/openjdk
 COPY --from=eclipse-temurin:22 $JAVA_HOME $JAVA_HOME
 ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
+RUN set -eux; \
 apt-get update && \
-apt-get install -y curl make git rlwrap && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
 clojure -e "(clojure-version)" && \
-apt-get purge -y --auto-remove curl
+apt-get purge -y --auto-remove curl gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009
diff --git a/target/debian-bullseye-slim-8/lein/Dockerfile b/target/debian-bullseye-slim-8/lein/Dockerfile
index 15ed6841..a5993e00 100644
--- a/target/debian-bullseye-slim-8/lein/Dockerfile
+++ b/target/debian-bullseye-slim-8/lein/Dockerfile
@@ -6,39 +6,48 @@ ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
 apt-get update && \
-apt-get install -y gnupg wget && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apt-get purge -y --auto-remove gnupg wget
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove curl gnupg
 
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 CMD ["lein", "repl"]
diff --git a/target/debian-bullseye-slim-8/lein/rlwrap.retry b/target/debian-bullseye-slim-8/lein/rlwrap.retry
new file mode 100755
index 00000000..83cefbfb
--- /dev/null
+++ b/target/debian-bullseye-slim-8/lein/rlwrap.retry
@@ -0,0 +1,30 @@
+#!/bin/sh
+
+# This script works around a Docker bug that prevents rlwrap from starting
+# right when a container is first started. It is intended to replace
+# /usr/bin/rlwrap and also be named rlwrap but earlier in the PATH
+# (e.g. /usr/local/bin).
+
+max_tries=100 # 100 tries is ~1 second
+try=0
+
+while true; do
+  # see if rlwrap can start at all
+  output=$(/usr/bin/rlwrap true 2>&1 >/dev/null)
+  exit_code=$?
+  if [ $exit_code -gt 0 ]; then
+    # it didn't start
+    try=$((try+1))
+    if [ $try -gt $max_tries ]; then
+      # we're at max attempts so output the error and exit w/ the same code
+      echo "$output" >&2
+      exit $exit_code
+    else
+      # wait a bit and try again
+      sleep 0.01
+    fi
+  else
+    # rlwrap can start so let's run it for real
+    exec /usr/bin/rlwrap "$@"
+  fi
+done
diff --git a/target/debian-bullseye-slim-8/tools-deps/Dockerfile b/target/debian-bullseye-slim-8/tools-deps/Dockerfile
index fecf3639..6fb481a9 100644
--- a/target/debian-bullseye-slim-8/tools-deps/Dockerfile
+++ b/target/debian-bullseye-slim-8/tools-deps/Dockerfile
@@ -4,22 +4,46 @@ ENV JAVA_HOME=/opt/java/openjdk
 COPY --from=eclipse-temurin:8 $JAVA_HOME $JAVA_HOME
 ENV PATH="${JAVA_HOME}/bin:${PATH}"
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
+RUN set -eux; \
 apt-get update && \
-apt-get install -y curl make git rlwrap && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
 clojure -e "(clojure-version)" && \
-apt-get purge -y --auto-remove curl
+apt-get purge -y --auto-remove curl gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009
diff --git a/target/eclipse-temurin-11-jdk-alpine/lein/Dockerfile b/target/eclipse-temurin-11-jdk-alpine/lein/Dockerfile
index 11863bdc..b739bb67 100644
--- a/target/eclipse-temurin-11-jdk-alpine/lein/Dockerfile
+++ b/target/eclipse-temurin-11-jdk-alpine/lein/Dockerfile
@@ -2,37 +2,46 @@ FROM eclipse-temurin:11-jdk-alpine
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
-apk add --no-cache ca-certificates bash tar openssl gnupg && \
+apk add --no-cache ca-certificates curl bash tar openssl make git gnupg && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apk del ca-certificates tar openssl gnupg
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apk del ca-certificates curl tar openssl gnupg
 
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 CMD ["lein", "repl"]
diff --git a/target/eclipse-temurin-11-jdk-alpine/lein/rlwrap.retry b/target/eclipse-temurin-11-jdk-alpine/lein/rlwrap.retry
new file mode 100755
index 00000000..83cefbfb
--- /dev/null
+++ b/target/eclipse-temurin-11-jdk-alpine/lein/rlwrap.retry
@@ -0,0 +1,30 @@
+#!/bin/sh
+
+# This script works around a Docker bug that prevents rlwrap from starting
+# right when a container is first started. It is intended to replace
+# /usr/bin/rlwrap and also be named rlwrap but earlier in the PATH
+# (e.g. /usr/local/bin).
+
+max_tries=100 # 100 tries is ~1 second
+try=0
+
+while true; do
+  # see if rlwrap can start at all
+  output=$(/usr/bin/rlwrap true 2>&1 >/dev/null)
+  exit_code=$?
+  if [ $exit_code -gt 0 ]; then
+    # it didn't start
+    try=$((try+1))
+    if [ $try -gt $max_tries ]; then
+      # we're at max attempts so output the error and exit w/ the same code
+      echo "$output" >&2
+      exit $exit_code
+    else
+      # wait a bit and try again
+      sleep 0.01
+    fi
+  else
+    # rlwrap can start so let's run it for real
+    exec /usr/bin/rlwrap "$@"
+  fi
+done
diff --git a/target/eclipse-temurin-11-jdk-alpine/tools-deps/Dockerfile b/target/eclipse-temurin-11-jdk-alpine/tools-deps/Dockerfile
index aaefb7b5..dc87ec5f 100644
--- a/target/eclipse-temurin-11-jdk-alpine/tools-deps/Dockerfile
+++ b/target/eclipse-temurin-11-jdk-alpine/tools-deps/Dockerfile
@@ -1,19 +1,43 @@
 FROM eclipse-temurin:11-jdk-alpine
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
-apk add --no-cache curl bash make git && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
+RUN set -eux; \
+apk add --no-cache ca-certificates curl bash tar openssl make git gnupg && \
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
 clojure -e "(clojure-version)" && \
-apk del curl
+apk del ca-certificates curl tar openssl gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009
diff --git a/target/eclipse-temurin-11-jdk-focal/lein/Dockerfile b/target/eclipse-temurin-11-jdk-focal/lein/Dockerfile
index e20f07cc..b7b8303a 100644
--- a/target/eclipse-temurin-11-jdk-focal/lein/Dockerfile
+++ b/target/eclipse-temurin-11-jdk-focal/lein/Dockerfile
@@ -2,39 +2,48 @@ FROM eclipse-temurin:11-jdk-focal
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
 apt-get update && \
-apt-get install -y make gnupg wget && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apt-get purge -y --auto-remove gnupg wget
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove gnupg
 
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 CMD ["lein", "repl"]
diff --git a/target/eclipse-temurin-11-jdk-focal/lein/rlwrap.retry b/target/eclipse-temurin-11-jdk-focal/lein/rlwrap.retry
new file mode 100755
index 00000000..83cefbfb
--- /dev/null
+++ b/target/eclipse-temurin-11-jdk-focal/lein/rlwrap.retry
@@ -0,0 +1,30 @@
+#!/bin/sh
+
+# This script works around a Docker bug that prevents rlwrap from starting
+# right when a container is first started. It is intended to replace
+# /usr/bin/rlwrap and also be named rlwrap but earlier in the PATH
+# (e.g. /usr/local/bin).
+
+max_tries=100 # 100 tries is ~1 second
+try=0
+
+while true; do
+  # see if rlwrap can start at all
+  output=$(/usr/bin/rlwrap true 2>&1 >/dev/null)
+  exit_code=$?
+  if [ $exit_code -gt 0 ]; then
+    # it didn't start
+    try=$((try+1))
+    if [ $try -gt $max_tries ]; then
+      # we're at max attempts so output the error and exit w/ the same code
+      echo "$output" >&2
+      exit $exit_code
+    else
+      # wait a bit and try again
+      sleep 0.01
+    fi
+  else
+    # rlwrap can start so let's run it for real
+    exec /usr/bin/rlwrap "$@"
+  fi
+done
diff --git a/target/eclipse-temurin-11-jdk-focal/tools-deps/Dockerfile b/target/eclipse-temurin-11-jdk-focal/tools-deps/Dockerfile
index df5ac2ba..96004d52 100644
--- a/target/eclipse-temurin-11-jdk-focal/tools-deps/Dockerfile
+++ b/target/eclipse-temurin-11-jdk-focal/tools-deps/Dockerfile
@@ -1,20 +1,45 @@
 FROM eclipse-temurin:11-jdk-focal
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
+RUN set -eux; \
 apt-get update && \
-apt-get install -y curl make git rlwrap && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
-clojure -e "(clojure-version)"
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009
diff --git a/target/eclipse-temurin-11-jdk-jammy/lein/Dockerfile b/target/eclipse-temurin-11-jdk-jammy/lein/Dockerfile
index 6d08b35b..36cc591d 100644
--- a/target/eclipse-temurin-11-jdk-jammy/lein/Dockerfile
+++ b/target/eclipse-temurin-11-jdk-jammy/lein/Dockerfile
@@ -2,39 +2,48 @@ FROM eclipse-temurin:11-jdk-jammy
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
 apt-get update && \
-apt-get install -y make gnupg wget && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apt-get purge -y --auto-remove gnupg wget
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove gnupg
 
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 CMD ["lein", "repl"]
diff --git a/target/eclipse-temurin-11-jdk-jammy/lein/rlwrap.retry b/target/eclipse-temurin-11-jdk-jammy/lein/rlwrap.retry
new file mode 100755
index 00000000..83cefbfb
--- /dev/null
+++ b/target/eclipse-temurin-11-jdk-jammy/lein/rlwrap.retry
@@ -0,0 +1,30 @@
+#!/bin/sh
+
+# This script works around a Docker bug that prevents rlwrap from starting
+# right when a container is first started. It is intended to replace
+# /usr/bin/rlwrap and also be named rlwrap but earlier in the PATH
+# (e.g. /usr/local/bin).
+
+max_tries=100 # 100 tries is ~1 second
+try=0
+
+while true; do
+  # see if rlwrap can start at all
+  output=$(/usr/bin/rlwrap true 2>&1 >/dev/null)
+  exit_code=$?
+  if [ $exit_code -gt 0 ]; then
+    # it didn't start
+    try=$((try+1))
+    if [ $try -gt $max_tries ]; then
+      # we're at max attempts so output the error and exit w/ the same code
+      echo "$output" >&2
+      exit $exit_code
+    else
+      # wait a bit and try again
+      sleep 0.01
+    fi
+  else
+    # rlwrap can start so let's run it for real
+    exec /usr/bin/rlwrap "$@"
+  fi
+done
diff --git a/target/eclipse-temurin-11-jdk-jammy/tools-deps/Dockerfile b/target/eclipse-temurin-11-jdk-jammy/tools-deps/Dockerfile
index 9b53c7d0..9922e197 100644
--- a/target/eclipse-temurin-11-jdk-jammy/tools-deps/Dockerfile
+++ b/target/eclipse-temurin-11-jdk-jammy/tools-deps/Dockerfile
@@ -1,20 +1,45 @@
 FROM eclipse-temurin:11-jdk-jammy
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
+RUN set -eux; \
 apt-get update && \
-apt-get install -y curl make git rlwrap && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
-clojure -e "(clojure-version)"
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009
diff --git a/target/eclipse-temurin-17-jdk-alpine/lein/Dockerfile b/target/eclipse-temurin-17-jdk-alpine/lein/Dockerfile
index 1683de42..53dceb8c 100644
--- a/target/eclipse-temurin-17-jdk-alpine/lein/Dockerfile
+++ b/target/eclipse-temurin-17-jdk-alpine/lein/Dockerfile
@@ -2,38 +2,47 @@ FROM eclipse-temurin:17-jdk-alpine
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
-apk add --no-cache ca-certificates bash tar openssl gnupg && \
+apk add --no-cache ca-certificates curl bash tar openssl make git gnupg && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apk del ca-certificates tar openssl gnupg
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apk del ca-certificates curl tar openssl gnupg
 
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 COPY entrypoint /usr/local/bin/entrypoint
 
diff --git a/target/eclipse-temurin-17-jdk-alpine/lein/rlwrap.retry b/target/eclipse-temurin-17-jdk-alpine/lein/rlwrap.retry
new file mode 100755
index 00000000..83cefbfb
--- /dev/null
+++ b/target/eclipse-temurin-17-jdk-alpine/lein/rlwrap.retry
@@ -0,0 +1,30 @@
+#!/bin/sh
+
+# This script works around a Docker bug that prevents rlwrap from starting
+# right when a container is first started. It is intended to replace
+# /usr/bin/rlwrap and also be named rlwrap but earlier in the PATH
+# (e.g. /usr/local/bin).
+
+max_tries=100 # 100 tries is ~1 second
+try=0
+
+while true; do
+  # see if rlwrap can start at all
+  output=$(/usr/bin/rlwrap true 2>&1 >/dev/null)
+  exit_code=$?
+  if [ $exit_code -gt 0 ]; then
+    # it didn't start
+    try=$((try+1))
+    if [ $try -gt $max_tries ]; then
+      # we're at max attempts so output the error and exit w/ the same code
+      echo "$output" >&2
+      exit $exit_code
+    else
+      # wait a bit and try again
+      sleep 0.01
+    fi
+  else
+    # rlwrap can start so let's run it for real
+    exec /usr/bin/rlwrap "$@"
+  fi
+done
diff --git a/target/eclipse-temurin-17-jdk-alpine/tools-deps/Dockerfile b/target/eclipse-temurin-17-jdk-alpine/tools-deps/Dockerfile
index fc758f39..7f70e86d 100644
--- a/target/eclipse-temurin-17-jdk-alpine/tools-deps/Dockerfile
+++ b/target/eclipse-temurin-17-jdk-alpine/tools-deps/Dockerfile
@@ -1,19 +1,43 @@
 FROM eclipse-temurin:17-jdk-alpine
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
-apk add --no-cache curl bash make git && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
+RUN set -eux; \
+apk add --no-cache ca-certificates curl bash tar openssl make git gnupg && \
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
 clojure -e "(clojure-version)" && \
-apk del curl
+apk del ca-certificates curl tar openssl gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009
diff --git a/target/eclipse-temurin-17-jdk-focal/lein/Dockerfile b/target/eclipse-temurin-17-jdk-focal/lein/Dockerfile
index abf29e08..81e990eb 100644
--- a/target/eclipse-temurin-17-jdk-focal/lein/Dockerfile
+++ b/target/eclipse-temurin-17-jdk-focal/lein/Dockerfile
@@ -2,40 +2,49 @@ FROM eclipse-temurin:17-jdk-focal
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
 apt-get update && \
-apt-get install -y make gnupg wget && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apt-get purge -y --auto-remove gnupg wget
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove gnupg
 
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 COPY entrypoint /usr/local/bin/entrypoint
 
diff --git a/target/eclipse-temurin-17-jdk-focal/lein/rlwrap.retry b/target/eclipse-temurin-17-jdk-focal/lein/rlwrap.retry
new file mode 100755
index 00000000..83cefbfb
--- /dev/null
+++ b/target/eclipse-temurin-17-jdk-focal/lein/rlwrap.retry
@@ -0,0 +1,30 @@
+#!/bin/sh
+
+# This script works around a Docker bug that prevents rlwrap from starting
+# right when a container is first started. It is intended to replace
+# /usr/bin/rlwrap and also be named rlwrap but earlier in the PATH
+# (e.g. /usr/local/bin).
+
+max_tries=100 # 100 tries is ~1 second
+try=0
+
+while true; do
+  # see if rlwrap can start at all
+  output=$(/usr/bin/rlwrap true 2>&1 >/dev/null)
+  exit_code=$?
+  if [ $exit_code -gt 0 ]; then
+    # it didn't start
+    try=$((try+1))
+    if [ $try -gt $max_tries ]; then
+      # we're at max attempts so output the error and exit w/ the same code
+      echo "$output" >&2
+      exit $exit_code
+    else
+      # wait a bit and try again
+      sleep 0.01
+    fi
+  else
+    # rlwrap can start so let's run it for real
+    exec /usr/bin/rlwrap "$@"
+  fi
+done
diff --git a/target/eclipse-temurin-17-jdk-focal/tools-deps/Dockerfile b/target/eclipse-temurin-17-jdk-focal/tools-deps/Dockerfile
index 56e5e6b9..4067e3ba 100644
--- a/target/eclipse-temurin-17-jdk-focal/tools-deps/Dockerfile
+++ b/target/eclipse-temurin-17-jdk-focal/tools-deps/Dockerfile
@@ -1,20 +1,45 @@
 FROM eclipse-temurin:17-jdk-focal
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
+RUN set -eux; \
 apt-get update && \
-apt-get install -y curl make git rlwrap && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
-clojure -e "(clojure-version)"
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009
diff --git a/target/eclipse-temurin-17-jdk-jammy/lein/Dockerfile b/target/eclipse-temurin-17-jdk-jammy/lein/Dockerfile
index 03f2de6d..fba63851 100644
--- a/target/eclipse-temurin-17-jdk-jammy/lein/Dockerfile
+++ b/target/eclipse-temurin-17-jdk-jammy/lein/Dockerfile
@@ -2,40 +2,49 @@ FROM eclipse-temurin:17-jdk-jammy
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
 apt-get update && \
-apt-get install -y make gnupg wget && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apt-get purge -y --auto-remove gnupg wget
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove gnupg
 
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 COPY entrypoint /usr/local/bin/entrypoint
 
diff --git a/target/eclipse-temurin-17-jdk-jammy/lein/rlwrap.retry b/target/eclipse-temurin-17-jdk-jammy/lein/rlwrap.retry
new file mode 100755
index 00000000..83cefbfb
--- /dev/null
+++ b/target/eclipse-temurin-17-jdk-jammy/lein/rlwrap.retry
@@ -0,0 +1,30 @@
+#!/bin/sh
+
+# This script works around a Docker bug that prevents rlwrap from starting
+# right when a container is first started. It is intended to replace
+# /usr/bin/rlwrap and also be named rlwrap but earlier in the PATH
+# (e.g. /usr/local/bin).
+
+max_tries=100 # 100 tries is ~1 second
+try=0
+
+while true; do
+  # see if rlwrap can start at all
+  output=$(/usr/bin/rlwrap true 2>&1 >/dev/null)
+  exit_code=$?
+  if [ $exit_code -gt 0 ]; then
+    # it didn't start
+    try=$((try+1))
+    if [ $try -gt $max_tries ]; then
+      # we're at max attempts so output the error and exit w/ the same code
+      echo "$output" >&2
+      exit $exit_code
+    else
+      # wait a bit and try again
+      sleep 0.01
+    fi
+  else
+    # rlwrap can start so let's run it for real
+    exec /usr/bin/rlwrap "$@"
+  fi
+done
diff --git a/target/eclipse-temurin-17-jdk-jammy/tools-deps/Dockerfile b/target/eclipse-temurin-17-jdk-jammy/tools-deps/Dockerfile
index 9e6ba548..331fe8a0 100644
--- a/target/eclipse-temurin-17-jdk-jammy/tools-deps/Dockerfile
+++ b/target/eclipse-temurin-17-jdk-jammy/tools-deps/Dockerfile
@@ -1,20 +1,45 @@
 FROM eclipse-temurin:17-jdk-jammy
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
+RUN set -eux; \
 apt-get update && \
-apt-get install -y curl make git rlwrap && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
-clojure -e "(clojure-version)"
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009
diff --git a/target/eclipse-temurin-21-jdk-alpine/lein/Dockerfile b/target/eclipse-temurin-21-jdk-alpine/lein/Dockerfile
index 3f5774a6..9a174d85 100644
--- a/target/eclipse-temurin-21-jdk-alpine/lein/Dockerfile
+++ b/target/eclipse-temurin-21-jdk-alpine/lein/Dockerfile
@@ -2,38 +2,47 @@ FROM eclipse-temurin:21-jdk-alpine
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
-apk add --no-cache ca-certificates bash tar openssl gnupg && \
+apk add --no-cache ca-certificates curl bash tar openssl make git gnupg && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apk del ca-certificates tar openssl gnupg
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apk del ca-certificates curl tar openssl gnupg
 
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 COPY entrypoint /usr/local/bin/entrypoint
 
diff --git a/target/eclipse-temurin-21-jdk-alpine/lein/rlwrap.retry b/target/eclipse-temurin-21-jdk-alpine/lein/rlwrap.retry
new file mode 100755
index 00000000..83cefbfb
--- /dev/null
+++ b/target/eclipse-temurin-21-jdk-alpine/lein/rlwrap.retry
@@ -0,0 +1,30 @@
+#!/bin/sh
+
+# This script works around a Docker bug that prevents rlwrap from starting
+# right when a container is first started. It is intended to replace
+# /usr/bin/rlwrap and also be named rlwrap but earlier in the PATH
+# (e.g. /usr/local/bin).
+
+max_tries=100 # 100 tries is ~1 second
+try=0
+
+while true; do
+  # see if rlwrap can start at all
+  output=$(/usr/bin/rlwrap true 2>&1 >/dev/null)
+  exit_code=$?
+  if [ $exit_code -gt 0 ]; then
+    # it didn't start
+    try=$((try+1))
+    if [ $try -gt $max_tries ]; then
+      # we're at max attempts so output the error and exit w/ the same code
+      echo "$output" >&2
+      exit $exit_code
+    else
+      # wait a bit and try again
+      sleep 0.01
+    fi
+  else
+    # rlwrap can start so let's run it for real
+    exec /usr/bin/rlwrap "$@"
+  fi
+done
diff --git a/target/eclipse-temurin-21-jdk-alpine/tools-deps/Dockerfile b/target/eclipse-temurin-21-jdk-alpine/tools-deps/Dockerfile
index 83e31e50..c91df61b 100644
--- a/target/eclipse-temurin-21-jdk-alpine/tools-deps/Dockerfile
+++ b/target/eclipse-temurin-21-jdk-alpine/tools-deps/Dockerfile
@@ -1,19 +1,43 @@
 FROM eclipse-temurin:21-jdk-alpine
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
-apk add --no-cache curl bash make git && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
+RUN set -eux; \
+apk add --no-cache ca-certificates curl bash tar openssl make git gnupg && \
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
 clojure -e "(clojure-version)" && \
-apk del curl
+apk del ca-certificates curl tar openssl gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009
diff --git a/target/eclipse-temurin-21-jdk-jammy/lein/Dockerfile b/target/eclipse-temurin-21-jdk-jammy/lein/Dockerfile
index 434fb8a4..037bfe12 100644
--- a/target/eclipse-temurin-21-jdk-jammy/lein/Dockerfile
+++ b/target/eclipse-temurin-21-jdk-jammy/lein/Dockerfile
@@ -2,40 +2,49 @@ FROM eclipse-temurin:21-jdk-jammy
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
 apt-get update && \
-apt-get install -y make gnupg wget && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apt-get purge -y --auto-remove gnupg wget
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove gnupg
 
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 COPY entrypoint /usr/local/bin/entrypoint
 
diff --git a/target/eclipse-temurin-21-jdk-jammy/lein/rlwrap.retry b/target/eclipse-temurin-21-jdk-jammy/lein/rlwrap.retry
new file mode 100755
index 00000000..83cefbfb
--- /dev/null
+++ b/target/eclipse-temurin-21-jdk-jammy/lein/rlwrap.retry
@@ -0,0 +1,30 @@
+#!/bin/sh
+
+# This script works around a Docker bug that prevents rlwrap from starting
+# right when a container is first started. It is intended to replace
+# /usr/bin/rlwrap and also be named rlwrap but earlier in the PATH
+# (e.g. /usr/local/bin).
+
+max_tries=100 # 100 tries is ~1 second
+try=0
+
+while true; do
+  # see if rlwrap can start at all
+  output=$(/usr/bin/rlwrap true 2>&1 >/dev/null)
+  exit_code=$?
+  if [ $exit_code -gt 0 ]; then
+    # it didn't start
+    try=$((try+1))
+    if [ $try -gt $max_tries ]; then
+      # we're at max attempts so output the error and exit w/ the same code
+      echo "$output" >&2
+      exit $exit_code
+    else
+      # wait a bit and try again
+      sleep 0.01
+    fi
+  else
+    # rlwrap can start so let's run it for real
+    exec /usr/bin/rlwrap "$@"
+  fi
+done
diff --git a/target/eclipse-temurin-21-jdk-jammy/tools-deps/Dockerfile b/target/eclipse-temurin-21-jdk-jammy/tools-deps/Dockerfile
index 0f975af9..5510c266 100644
--- a/target/eclipse-temurin-21-jdk-jammy/tools-deps/Dockerfile
+++ b/target/eclipse-temurin-21-jdk-jammy/tools-deps/Dockerfile
@@ -1,20 +1,45 @@
 FROM eclipse-temurin:21-jdk-jammy
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
+RUN set -eux; \
 apt-get update && \
-apt-get install -y curl make git rlwrap && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
-clojure -e "(clojure-version)"
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009
diff --git a/target/eclipse-temurin-22-jdk-alpine/lein/Dockerfile b/target/eclipse-temurin-22-jdk-alpine/lein/Dockerfile
index 3af1f17e..f1a92497 100644
--- a/target/eclipse-temurin-22-jdk-alpine/lein/Dockerfile
+++ b/target/eclipse-temurin-22-jdk-alpine/lein/Dockerfile
@@ -2,38 +2,47 @@ FROM eclipse-temurin:22-jdk-alpine
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
-apk add --no-cache ca-certificates bash tar openssl gnupg && \
+apk add --no-cache ca-certificates curl bash tar openssl make git gnupg && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apk del ca-certificates tar openssl gnupg
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apk del ca-certificates curl tar openssl gnupg
 
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 COPY entrypoint /usr/local/bin/entrypoint
 
diff --git a/target/eclipse-temurin-22-jdk-alpine/lein/rlwrap.retry b/target/eclipse-temurin-22-jdk-alpine/lein/rlwrap.retry
new file mode 100755
index 00000000..83cefbfb
--- /dev/null
+++ b/target/eclipse-temurin-22-jdk-alpine/lein/rlwrap.retry
@@ -0,0 +1,30 @@
+#!/bin/sh
+
+# This script works around a Docker bug that prevents rlwrap from starting
+# right when a container is first started. It is intended to replace
+# /usr/bin/rlwrap and also be named rlwrap but earlier in the PATH
+# (e.g. /usr/local/bin).
+
+max_tries=100 # 100 tries is ~1 second
+try=0
+
+while true; do
+  # see if rlwrap can start at all
+  output=$(/usr/bin/rlwrap true 2>&1 >/dev/null)
+  exit_code=$?
+  if [ $exit_code -gt 0 ]; then
+    # it didn't start
+    try=$((try+1))
+    if [ $try -gt $max_tries ]; then
+      # we're at max attempts so output the error and exit w/ the same code
+      echo "$output" >&2
+      exit $exit_code
+    else
+      # wait a bit and try again
+      sleep 0.01
+    fi
+  else
+    # rlwrap can start so let's run it for real
+    exec /usr/bin/rlwrap "$@"
+  fi
+done
diff --git a/target/eclipse-temurin-22-jdk-alpine/tools-deps/Dockerfile b/target/eclipse-temurin-22-jdk-alpine/tools-deps/Dockerfile
index 35a947cc..0abf3703 100644
--- a/target/eclipse-temurin-22-jdk-alpine/tools-deps/Dockerfile
+++ b/target/eclipse-temurin-22-jdk-alpine/tools-deps/Dockerfile
@@ -1,19 +1,43 @@
 FROM eclipse-temurin:22-jdk-alpine
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
-apk add --no-cache curl bash make git && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
+RUN set -eux; \
+apk add --no-cache ca-certificates curl bash tar openssl make git gnupg && \
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
 clojure -e "(clojure-version)" && \
-apk del curl
+apk del ca-certificates curl tar openssl gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009
diff --git a/target/eclipse-temurin-22-jdk-jammy/lein/Dockerfile b/target/eclipse-temurin-22-jdk-jammy/lein/Dockerfile
index 63a02944..0dff9ddf 100644
--- a/target/eclipse-temurin-22-jdk-jammy/lein/Dockerfile
+++ b/target/eclipse-temurin-22-jdk-jammy/lein/Dockerfile
@@ -2,40 +2,49 @@ FROM eclipse-temurin:22-jdk-jammy
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
 apt-get update && \
-apt-get install -y make gnupg wget && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apt-get purge -y --auto-remove gnupg wget
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove gnupg
 
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 COPY entrypoint /usr/local/bin/entrypoint
 
diff --git a/target/eclipse-temurin-22-jdk-jammy/lein/rlwrap.retry b/target/eclipse-temurin-22-jdk-jammy/lein/rlwrap.retry
new file mode 100755
index 00000000..83cefbfb
--- /dev/null
+++ b/target/eclipse-temurin-22-jdk-jammy/lein/rlwrap.retry
@@ -0,0 +1,30 @@
+#!/bin/sh
+
+# This script works around a Docker bug that prevents rlwrap from starting
+# right when a container is first started. It is intended to replace
+# /usr/bin/rlwrap and also be named rlwrap but earlier in the PATH
+# (e.g. /usr/local/bin).
+
+max_tries=100 # 100 tries is ~1 second
+try=0
+
+while true; do
+  # see if rlwrap can start at all
+  output=$(/usr/bin/rlwrap true 2>&1 >/dev/null)
+  exit_code=$?
+  if [ $exit_code -gt 0 ]; then
+    # it didn't start
+    try=$((try+1))
+    if [ $try -gt $max_tries ]; then
+      # we're at max attempts so output the error and exit w/ the same code
+      echo "$output" >&2
+      exit $exit_code
+    else
+      # wait a bit and try again
+      sleep 0.01
+    fi
+  else
+    # rlwrap can start so let's run it for real
+    exec /usr/bin/rlwrap "$@"
+  fi
+done
diff --git a/target/eclipse-temurin-22-jdk-jammy/tools-deps/Dockerfile b/target/eclipse-temurin-22-jdk-jammy/tools-deps/Dockerfile
index ae6a1e1e..b7ba50f5 100644
--- a/target/eclipse-temurin-22-jdk-jammy/tools-deps/Dockerfile
+++ b/target/eclipse-temurin-22-jdk-jammy/tools-deps/Dockerfile
@@ -1,20 +1,45 @@
 FROM eclipse-temurin:22-jdk-jammy
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
+RUN set -eux; \
 apt-get update && \
-apt-get install -y curl make git rlwrap && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
-clojure -e "(clojure-version)"
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009
diff --git a/target/eclipse-temurin-8-jdk-alpine/lein/Dockerfile b/target/eclipse-temurin-8-jdk-alpine/lein/Dockerfile
index 40a51d4e..903e70cc 100644
--- a/target/eclipse-temurin-8-jdk-alpine/lein/Dockerfile
+++ b/target/eclipse-temurin-8-jdk-alpine/lein/Dockerfile
@@ -2,37 +2,46 @@ FROM eclipse-temurin:8-jdk-alpine
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
-apk add --no-cache ca-certificates bash tar openssl gnupg && \
+apk add --no-cache ca-certificates curl bash tar openssl make git gnupg && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apk del ca-certificates tar openssl gnupg
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apk del ca-certificates curl tar openssl gnupg
 
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 CMD ["lein", "repl"]
diff --git a/target/eclipse-temurin-8-jdk-alpine/lein/rlwrap.retry b/target/eclipse-temurin-8-jdk-alpine/lein/rlwrap.retry
new file mode 100755
index 00000000..83cefbfb
--- /dev/null
+++ b/target/eclipse-temurin-8-jdk-alpine/lein/rlwrap.retry
@@ -0,0 +1,30 @@
+#!/bin/sh
+
+# This script works around a Docker bug that prevents rlwrap from starting
+# right when a container is first started. It is intended to replace
+# /usr/bin/rlwrap and also be named rlwrap but earlier in the PATH
+# (e.g. /usr/local/bin).
+
+max_tries=100 # 100 tries is ~1 second
+try=0
+
+while true; do
+  # see if rlwrap can start at all
+  output=$(/usr/bin/rlwrap true 2>&1 >/dev/null)
+  exit_code=$?
+  if [ $exit_code -gt 0 ]; then
+    # it didn't start
+    try=$((try+1))
+    if [ $try -gt $max_tries ]; then
+      # we're at max attempts so output the error and exit w/ the same code
+      echo "$output" >&2
+      exit $exit_code
+    else
+      # wait a bit and try again
+      sleep 0.01
+    fi
+  else
+    # rlwrap can start so let's run it for real
+    exec /usr/bin/rlwrap "$@"
+  fi
+done
diff --git a/target/eclipse-temurin-8-jdk-alpine/tools-deps/Dockerfile b/target/eclipse-temurin-8-jdk-alpine/tools-deps/Dockerfile
index 2bc521eb..0962cc60 100644
--- a/target/eclipse-temurin-8-jdk-alpine/tools-deps/Dockerfile
+++ b/target/eclipse-temurin-8-jdk-alpine/tools-deps/Dockerfile
@@ -1,19 +1,43 @@
 FROM eclipse-temurin:8-jdk-alpine
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
-apk add --no-cache curl bash make git && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
+RUN set -eux; \
+apk add --no-cache ca-certificates curl bash tar openssl make git gnupg && \
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
 clojure -e "(clojure-version)" && \
-apk del curl
+apk del ca-certificates curl tar openssl gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009
diff --git a/target/eclipse-temurin-8-jdk-focal/lein/Dockerfile b/target/eclipse-temurin-8-jdk-focal/lein/Dockerfile
index b1065f94..364b5b41 100644
--- a/target/eclipse-temurin-8-jdk-focal/lein/Dockerfile
+++ b/target/eclipse-temurin-8-jdk-focal/lein/Dockerfile
@@ -2,39 +2,48 @@ FROM eclipse-temurin:8-jdk-focal
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
 apt-get update && \
-apt-get install -y make gnupg wget && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apt-get purge -y --auto-remove gnupg wget
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove gnupg
 
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 CMD ["lein", "repl"]
diff --git a/target/eclipse-temurin-8-jdk-focal/lein/rlwrap.retry b/target/eclipse-temurin-8-jdk-focal/lein/rlwrap.retry
new file mode 100755
index 00000000..83cefbfb
--- /dev/null
+++ b/target/eclipse-temurin-8-jdk-focal/lein/rlwrap.retry
@@ -0,0 +1,30 @@
+#!/bin/sh
+
+# This script works around a Docker bug that prevents rlwrap from starting
+# right when a container is first started. It is intended to replace
+# /usr/bin/rlwrap and also be named rlwrap but earlier in the PATH
+# (e.g. /usr/local/bin).
+
+max_tries=100 # 100 tries is ~1 second
+try=0
+
+while true; do
+  # see if rlwrap can start at all
+  output=$(/usr/bin/rlwrap true 2>&1 >/dev/null)
+  exit_code=$?
+  if [ $exit_code -gt 0 ]; then
+    # it didn't start
+    try=$((try+1))
+    if [ $try -gt $max_tries ]; then
+      # we're at max attempts so output the error and exit w/ the same code
+      echo "$output" >&2
+      exit $exit_code
+    else
+      # wait a bit and try again
+      sleep 0.01
+    fi
+  else
+    # rlwrap can start so let's run it for real
+    exec /usr/bin/rlwrap "$@"
+  fi
+done
diff --git a/target/eclipse-temurin-8-jdk-focal/tools-deps/Dockerfile b/target/eclipse-temurin-8-jdk-focal/tools-deps/Dockerfile
index e87147bf..c7a5d974 100644
--- a/target/eclipse-temurin-8-jdk-focal/tools-deps/Dockerfile
+++ b/target/eclipse-temurin-8-jdk-focal/tools-deps/Dockerfile
@@ -1,20 +1,45 @@
 FROM eclipse-temurin:8-jdk-focal
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
+RUN set -eux; \
 apt-get update && \
-apt-get install -y curl make git rlwrap && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
-clojure -e "(clojure-version)"
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009
diff --git a/target/eclipse-temurin-8-jdk-jammy/lein/Dockerfile b/target/eclipse-temurin-8-jdk-jammy/lein/Dockerfile
index 3027a5c5..52645486 100644
--- a/target/eclipse-temurin-8-jdk-jammy/lein/Dockerfile
+++ b/target/eclipse-temurin-8-jdk-jammy/lein/Dockerfile
@@ -2,39 +2,48 @@ FROM eclipse-temurin:8-jdk-jammy
 
 ENV LEIN_VERSION=2.11.2
 ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-# Download the whole repo as an archive
 RUN set -eux; \
 apt-get update && \
-apt-get install -y make gnupg wget && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
+echo Installing Leiningen && \
 mkdir -p $LEIN_INSTALL && \
-wget -q https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
 echo "Comparing lein-pkg checksum ..." && \
 sha256sum lein-pkg && \
 echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
 mv lein-pkg $LEIN_INSTALL/lein && \
 chmod 0755 $LEIN_INSTALL/lein && \
 export GNUPGHOME="$(mktemp -d)" && \
-export FILENAME_EXT=jar && \
 gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
-wget -q https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
-echo "Verifying file PGP signature..." && \
-gpg --batch --verify leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
 gpgconf --kill all && \
-rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT.asc && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
 mkdir -p /usr/share/java && \
-mv leiningen-$LEIN_VERSION-standalone.$FILENAME_EXT /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
-apt-get purge -y --auto-remove gnupg wget
-
-ENV PATH=$PATH:$LEIN_INSTALL
-ENV LEIN_ROOT 1
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove gnupg
 
-# Install clojure 1.11.1 so users don't have to download it every time
-RUN echo '(defproject dummy "" :dependencies [[org.clojure/clojure "1.11.1"]])' > project.clj \
-  && lein deps && rm project.clj
+# Docker bug makes rlwrap crash w/o short sleep first
+# Bug: https://github.com/moby/moby/issues/28009
+# As of 2021-09-10 this bug still exists, despite that issue being closed
+COPY rlwrap.retry /usr/local/bin/rlwrap
 
 CMD ["lein", "repl"]
diff --git a/target/eclipse-temurin-8-jdk-jammy/lein/rlwrap.retry b/target/eclipse-temurin-8-jdk-jammy/lein/rlwrap.retry
new file mode 100755
index 00000000..83cefbfb
--- /dev/null
+++ b/target/eclipse-temurin-8-jdk-jammy/lein/rlwrap.retry
@@ -0,0 +1,30 @@
+#!/bin/sh
+
+# This script works around a Docker bug that prevents rlwrap from starting
+# right when a container is first started. It is intended to replace
+# /usr/bin/rlwrap and also be named rlwrap but earlier in the PATH
+# (e.g. /usr/local/bin).
+
+max_tries=100 # 100 tries is ~1 second
+try=0
+
+while true; do
+  # see if rlwrap can start at all
+  output=$(/usr/bin/rlwrap true 2>&1 >/dev/null)
+  exit_code=$?
+  if [ $exit_code -gt 0 ]; then
+    # it didn't start
+    try=$((try+1))
+    if [ $try -gt $max_tries ]; then
+      # we're at max attempts so output the error and exit w/ the same code
+      echo "$output" >&2
+      exit $exit_code
+    else
+      # wait a bit and try again
+      sleep 0.01
+    fi
+  else
+    # rlwrap can start so let's run it for real
+    exec /usr/bin/rlwrap "$@"
+  fi
+done
diff --git a/target/eclipse-temurin-8-jdk-jammy/tools-deps/Dockerfile b/target/eclipse-temurin-8-jdk-jammy/tools-deps/Dockerfile
index 57434f3d..384186b9 100644
--- a/target/eclipse-temurin-8-jdk-jammy/tools-deps/Dockerfile
+++ b/target/eclipse-temurin-8-jdk-jammy/tools-deps/Dockerfile
@@ -1,20 +1,45 @@
 FROM eclipse-temurin:8-jdk-jammy
 
-ENV CLOJURE_VERSION=1.11.1.1435
+ENV LEIN_VERSION=2.11.2
+ENV LEIN_INSTALL=/usr/local/bin/
+ENV LEIN_ROOT=1
+ENV PATH=$PATH:$LEIN_INSTALL
+ENV CLOJURE_CLI_VERSION=1.11.1.1435
 
 WORKDIR /tmp
 
-RUN \
+RUN set -eux; \
 apt-get update && \
-apt-get install -y curl make git rlwrap && \
+apt-get install -y curl make git rlwrap gnupg && \
 rm -rf /var/lib/apt/lists/* && \
-curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_VERSION.sh && \
-sha256sum linux-install-$CLOJURE_VERSION.sh && \
-echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_VERSION.sh" | sha256sum -c - && \
-chmod +x linux-install-$CLOJURE_VERSION.sh && \
-./linux-install-$CLOJURE_VERSION.sh && \
-rm linux-install-$CLOJURE_VERSION.sh && \
-clojure -e "(clojure-version)"
+echo Installing Leiningen && \
+mkdir -p $LEIN_INSTALL && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/raw/tag/$LEIN_VERSION/bin/lein-pkg && \
+echo "Comparing lein-pkg checksum ..." && \
+sha256sum lein-pkg && \
+echo "28a1a62668c5f427b413a8677e376affaa995f023b1fcd06e2d4c98ac1df5f3e *lein-pkg" | sha256sum -c - && \
+mv lein-pkg $LEIN_INSTALL/lein && \
+chmod 0755 $LEIN_INSTALL/lein && \
+export GNUPGHOME="$(mktemp -d)" && \
+gpg --batch --keyserver hkps://keyserver.ubuntu.com --recv-keys 9D13D9426A0814B3373CF5E3D8A8243577A7859F && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar && \
+curl -fsSLO https://codeberg.org/leiningen/leiningen/releases/download/$LEIN_VERSION/leiningen-$LEIN_VERSION-standalone.jar.asc && \
+echo "Verifying Leiningen file PGP signature..." && \
+gpg --batch --verify leiningen-$LEIN_VERSION-standalone.jar.asc leiningen-$LEIN_VERSION-standalone.jar && \
+gpgconf --kill all && \
+rm -rf "$GNUPGHOME" leiningen-$LEIN_VERSION-standalone.jar.asc && \
+mkdir -p /usr/share/java && \
+mv leiningen-$LEIN_VERSION-standalone.jar /usr/share/java/leiningen-$LEIN_VERSION-standalone.jar && \
+mkdir -p ~/.lein/ && \
+echo Installing tools.deps && \
+curl -fsSLO https://download.clojure.org/install/linux-install-$CLOJURE_CLI_VERSION.sh && \
+sha256sum linux-install-$CLOJURE_CLI_VERSION.sh && \
+echo "7edee5b12197a2dbe6338e672b109b18164cde84bea1f049ceceed41fc4dd10a *linux-install-$CLOJURE_CLI_VERSION.sh" | sha256sum -c - && \
+chmod +x linux-install-$CLOJURE_CLI_VERSION.sh && \
+./linux-install-$CLOJURE_CLI_VERSION.sh && \
+rm linux-install-$CLOJURE_CLI_VERSION.sh && \
+clojure -e "(clojure-version)" && \
+apt-get purge -y --auto-remove gnupg
 
 # Docker bug makes rlwrap crash w/o short sleep first
 # Bug: https://github.com/moby/moby/issues/28009