diff --git a/deploy/Dockerfile b/deploy/Dockerfile
index 18a126410b..5f28ba212c 100644
--- a/deploy/Dockerfile
+++ b/deploy/Dockerfile
@@ -1,4 +1,4 @@
-FROM debian:bullseye-slim
+FROM debian:bookworm-slim
 
 RUN apt-get update && apt-get install -y --no-install-recommends \
     curl ca-certificates git gnupg2 s3cmd \
diff --git a/deploy/okteto/okteto.Dockerfile b/deploy/okteto/okteto.Dockerfile
index 4f281322f2..c8d9a1df63 100644
--- a/deploy/okteto/okteto.Dockerfile
+++ b/deploy/okteto/okteto.Dockerfile
@@ -1,5 +1,5 @@
 # syntax=docker/dockerfile:1.3
-FROM golang:1.20-bullseye as builder
+FROM golang:1.20-bookworm as builder
 
 EXPOSE 2345
 
diff --git a/hack/dev/skaffold.Dockerfile b/hack/dev/skaffold.Dockerfile
index e70ac942bb..51dbb96753 100644
--- a/hack/dev/skaffold.Dockerfile
+++ b/hack/dev/skaffold.Dockerfile
@@ -14,7 +14,7 @@ ARG DEBUG_KOTSADM=0
 
 RUN make build kots
 
-FROM debian:bullseye
+FROM debian:bookworm
 
 RUN apt-get update && apt-get install -y --no-install-recommends curl gnupg2 \
   && apt-get update && apt-get install -y --no-install-recommends git \
diff --git a/kurl_proxy/deploy/Dockerfile b/kurl_proxy/deploy/Dockerfile
index fec52d5ebd..14a2b82217 100644
--- a/kurl_proxy/deploy/Dockerfile
+++ b/kurl_proxy/deploy/Dockerfile
@@ -1,4 +1,4 @@
-FROM debian:bullseye-slim
+FROM debian:bookworm-slim
 
 ENV DEBIAN_FRONTEND=noninteractive
 
diff --git a/migrations/deploy/Dockerfile b/migrations/deploy/Dockerfile
index 6559a3e1d6..08ee5c113a 100644
--- a/migrations/deploy/Dockerfile
+++ b/migrations/deploy/Dockerfile
@@ -2,7 +2,7 @@ ARG SCHEMAHERO_TAG
 
 FROM schemahero/schemahero:${SCHEMAHERO_TAG} AS base
 
-FROM debian:bullseye
+FROM debian:bookworm
 WORKDIR /
 
 COPY --from=base /schemahero /schemahero
diff --git a/web/okteto.Dockerfile b/web/okteto.Dockerfile
index 7e824221c4..b13fc5365f 100644
--- a/web/okteto.Dockerfile
+++ b/web/okteto.Dockerfile
@@ -1,5 +1,5 @@
 # syntax=docker/dockerfile:1.3
-FROM node:18-bullseye-slim as dev
+FROM node:18-bookworm-slim as dev
 EXPOSE 8080 9229
 
 WORKDIR /src