diff --git a/.github/workflows/unstable.yml b/.github/workflows/unstable.yml
index 3dbad53..769ac16 100644
--- a/.github/workflows/unstable.yml
+++ b/.github/workflows/unstable.yml
@@ -27,7 +27,7 @@ jobs:
       - name: Prosody repo
         uses: myci-actions/add-deb-repo@11
         with:
-          repo: deb https://packages.prosody.im/debian bullseye main
+          repo: deb https://packages.prosody.im/debian bookworm main
           repo-name: prosody
           keys-asc: https://prosody.im/files/prosody-debian-packages.key
       - name: Jitsi repo
diff --git a/Makefile b/Makefile
index 2bb1842..cc05716 100644
--- a/Makefile
+++ b/Makefile
@@ -57,7 +57,6 @@ clean:
 	docker network prune
 
 prepare:
-	docker pull debian:bullseye-slim
 	FORCE_REBUILD=1 $(MAKE)
 
 .PHONY: all build tag push clean prepare release $(addprefix build_,$(JITSI_SERVICES))
diff --git a/base/Dockerfile b/base/Dockerfile
index 847bfe7..463bd21 100644
--- a/base/Dockerfile
+++ b/base/Dockerfile
@@ -1,4 +1,4 @@
-FROM docker.io/library/debian:bullseye-slim
+FROM docker.io/library/debian:bookworm-slim
 
 ARG JITSI_RELEASE=stable
 ENV S6_BEHAVIOUR_IF_STAGE2_FAILS=2
@@ -15,10 +15,17 @@ RUN \
     apt-dpkg-wrap apt-get update && \
     apt-dpkg-wrap apt-get install -y apt-transport-https apt-utils ca-certificates gnupg wget && \
     wget -qO /usr/bin/tpl https://github.com/jitsi/tpl/releases/download/v1.1.1/tpl-linux-${TPL_ARCH} && \
-    wget -qO - https://github.com/just-containers/s6-overlay/releases/download/v1.22.1.0/s6-overlay-${S6_ARCH}.tar.gz | tar xfz - -C / && \
+    # Workaround S6 bug when /bin is a symlink
+    wget -qO /tmp/s6.tar.gz https://github.com/just-containers/s6-overlay/releases/download/v1.22.1.0/s6-overlay-${S6_ARCH}.tar.gz && \
+    mkdir /tmp/s6 && \
+    tar xfz /tmp/s6.tar.gz -C /tmp/s6 && \
+    tar hxfz /tmp/s6.tar.gz -C / && \
+    rm -f /usr/bin/execlineb && \
+    cp /tmp/s6/bin/execlineb /usr/bin/ && \
+    rm -rf /tmp/s6* && \
     wget -qO - https://download.jitsi.org/jitsi-key.gpg.key | gpg --dearmour > /etc/apt/trusted.gpg.d/jitsi.gpg && \
     echo "deb https://download.jitsi.org $JITSI_RELEASE/" > /etc/apt/sources.list.d/jitsi.list && \
-    echo "deb http://ftp.debian.org/debian bullseye-backports main" > /etc/apt/sources.list.d/backports.list && \
+    echo "deb http://ftp.debian.org/debian bookworm-backports main" > /etc/apt/sources.list.d/backports.list && \
     apt-dpkg-wrap apt-get update && \
     apt-dpkg-wrap apt-get dist-upgrade -y && \
     apt-cleanup && \
diff --git a/prosody/Dockerfile b/prosody/Dockerfile
index f6542b6..d2eeb6a 100644
--- a/prosody/Dockerfile
+++ b/prosody/Dockerfile
@@ -31,7 +31,7 @@ ARG VERSION_JITSI_CONTRIB_PROSODY_PLUGINS="20240117"
 ARG VERSION_MATRIX_USER_VERIFICATION_SERVICE_PLUGIN="1.8.0"
 
 RUN wget -qO /etc/apt/trusted.gpg.d/prosody.gpg https://prosody.im/files/prosody-debian-packages.key && \
-    echo "deb http://packages.prosody.im/debian bullseye main" > /etc/apt/sources.list.d/prosody.list && \
+    echo "deb http://packages.prosody.im/debian bookworm main" > /etc/apt/sources.list.d/prosody.list && \
     apt-dpkg-wrap apt-get update && \
     apt-dpkg-wrap apt-get install -y \
       lua5.4 \