diff --git a/.cirrus.yml b/.cirrus.yml
index b3719430..d89c32f8 100644
--- a/.cirrus.yml
+++ b/.cirrus.yml
@@ -63,18 +63,18 @@ clang_tidy_task:
   << : *UNIX_ENV
   << : *BRANCH_WHITELIST
 
-fedora38_task:
+fedora39_task:
   container:
-    # Fedora 38 EOL: Around May 2024
-    dockerfile: ci/fedora-38/Dockerfile
+    # Fedora 39 EOL: Around Nov 2024
+    dockerfile: ci/fedora-39/Dockerfile
     << : *RESOURCES_TEMPLATE
   << : *CI_TEMPLATE
   << : *UNIX_ENV
 
-fedora37_task:
+fedora38_task:
   container:
-    # Fedora 37 EOL: Around Dec 2023
-    dockerfile: ci/fedora-37/Dockerfile
+    # Fedora 38 EOL: Around May 2024
+    dockerfile: ci/fedora-38/Dockerfile
     << : *RESOURCES_TEMPLATE
   << : *CI_TEMPLATE
   << : *UNIX_ENV
@@ -135,18 +135,18 @@ opensuse_leap_15_5_task:
   << : *CI_TEMPLATE
   << : *UNIX_ENV
 
-opensuse_leap_15_4_task:
+opensuse_tumbleweed_task:
   container:
-    # Opensuse Leap 15.4 EOL: ~Nov 2023
-    dockerfile: ci/opensuse-leap-15.4/Dockerfile
+    # Opensuse Tumbleweed has no EOL
+    dockerfile: ci/opensuse-tumbleweed/Dockerfile
     << : *RESOURCES_TEMPLATE
   << : *CI_TEMPLATE
   << : *UNIX_ENV
 
-opensuse_tumbleweed_task:
+ubuntu23_task:
   container:
-    # Opensuse Tumbleweed has no EOL
-    dockerfile: ci/opensuse-tumbleweed/Dockerfile
+    # Ubuntu 23.10 EOL: July 2024
+    dockerfile: ci/ubuntu-23.10/Dockerfile
     << : *RESOURCES_TEMPLATE
   << : *CI_TEMPLATE
   << : *UNIX_ENV
@@ -179,16 +179,16 @@ alpine_task:
 
 # Apple doesn't publish official long-term support timelines.
 # We aim to support both the current and previous macOS release.
-macos_ventura_task:
+macos_sonoma_task:
   macos_instance:
-    image: ghcr.io/cirruslabs/macos-ventura-base:latest
+    image: ghcr.io/cirruslabs/macos-sonoma-base:latest
   prepare_script: ./ci/macos/prepare.sh
   << : *CI_TEMPLATE
   << : *MACOS_RESOURCES_TEMPLATE
 
-macos_monterey_task:
+macos_ventura_task:
   macos_instance:
-    image: ghcr.io/cirruslabs/macos-monterey-base:latest
+    image: ghcr.io/cirruslabs/macos-ventura-base:latest
   prepare_script: ./ci/macos/prepare.sh
   << : *CI_TEMPLATE
   << : *MACOS_RESOURCES_TEMPLATE
@@ -196,15 +196,11 @@ macos_monterey_task:
 # FreeBSD EOL timelines: https://www.freebsd.org/security/#sup
 freebsd14_task:
   freebsd_instance:
-    # We don't support FreeBSD 14 yet, this is a purely informative task
-    image_family: freebsd-14-0-snap
+    # FreeBSD 14 EOL: Nov 30 2028
+    image_family: freebsd-14-0
     cpu: 8
     # Not allowed to request less than 8GB for an 8 CPU FreeBSD VM.
     memory: 8GB
-
-    allow_failures: true
-    skip_notification: true
-
   prepare_script: ./ci/freebsd/prepare.sh
   << : *CI_TEMPLATE
   << : *UNIX_ENV
@@ -212,18 +208,7 @@ freebsd14_task:
 freebsd13_task:
   freebsd_instance:
     # FreeBSD 13 EOL: January 31, 2026
-    image_family: freebsd-13-1
-    cpu: 8
-    # Not allowed to request less than 8GB for an 8 CPU FreeBSD VM.
-    memory: 8GB
-  prepare_script: ./ci/freebsd/prepare.sh
-  << : *CI_TEMPLATE
-  << : *UNIX_ENV
-
-freebsd12_task:
-  freebsd_instance:
-    # FreeBSD 12 EOL: June 30, 2024
-    image_family: freebsd-12-2
+    image_family: freebsd-13-2
     cpu: 8
     # Not allowed to request less than 8GB for an 8 CPU FreeBSD VM.
     memory: 8GB
diff --git a/ci/fedora-37/Dockerfile b/ci/fedora-39/Dockerfile
similarity index 88%
rename from ci/fedora-37/Dockerfile
rename to ci/fedora-39/Dockerfile
index 80b480cc..1cabc56b 100644
--- a/ci/fedora-37/Dockerfile
+++ b/ci/fedora-39/Dockerfile
@@ -1,8 +1,8 @@
-FROM fedora:37
+FROM fedora:39
 
 # A version field to invalidate Cirrus's build cache when needed, as suggested in
 # https://github.com/cirruslabs/cirrus-ci-docs/issues/544#issuecomment-566066822
-ENV DOCKERFILE_VERSION 20230813
+ENV DOCKERFILE_VERSION 20231213
 
 RUN dnf -y install \
     cmake \
diff --git a/ci/opensuse-leap-15.4/Dockerfile b/ci/opensuse-leap-15.4/Dockerfile
deleted file mode 100644
index 819ec392..00000000
--- a/ci/opensuse-leap-15.4/Dockerfile
+++ /dev/null
@@ -1,22 +0,0 @@
-FROM opensuse/leap:15.4
-
-# A version field to invalidate Cirrus's build cache when needed, as suggested in
-# https://github.com/cirruslabs/cirrus-ci-docs/issues/544#issuecomment-566066822
-ENV DOCKERFILE_VERSION 20220615
-
-RUN zypper in -y \
-    cmake \
-    gcc \
-    gcc-c++ \
-    git \
-    gzip \
-    libopenssl-devel \
-    make \
-    python39 \
-    python39-devel \
-    python39-pip \
-    tar \
-  && rm -rf /var/cache/zypp
-
-RUN update-alternatives --install /usr/bin/pip3 pip3 /usr/bin/pip3.9 100
-RUN update-alternatives --install /usr/bin/python3 python3 /usr/bin/python3.9 100
diff --git a/ci/ubuntu-23.10/Dockerfile b/ci/ubuntu-23.10/Dockerfile
new file mode 100644
index 00000000..47c16ca6
--- /dev/null
+++ b/ci/ubuntu-23.10/Dockerfile
@@ -0,0 +1,18 @@
+FROM ubuntu:23.10
+
+ENV DEBIAN_FRONTEND="noninteractive" TZ="America/Los_Angeles"
+
+# A version field to invalidate Cirrus's build cache when needed, as suggested in
+# https://github.com/cirruslabs/cirrus-ci-docs/issues/544#issuecomment-566066822
+ENV DOCKERFILE_VERSION 20231213
+
+RUN apt-get update && apt-get -y install \
+    cmake \
+    g++ \
+    git \
+    libssl-dev \
+    make \
+    python3 \
+    python3-dev \
+  && apt autoclean \
+  && rm -rf /var/lib/apt/lists/*