diff --git a/docker/Dockerfile b/docker/Dockerfile
index bdbc213..87a1584 100644
--- a/docker/Dockerfile
+++ b/docker/Dockerfile
@@ -2,7 +2,7 @@
 # Nginx Builder
 #############
 
-FROM debian:buster-slim as nginxbuilder
+FROM debian:bookworm-slim as nginxbuilder
 
 ARG OPENRESTY_VERSION
 ARG LUA_VERSION
@@ -33,13 +33,13 @@ RUN /tmp/build-openresty
 # Final Image
 #############
 
-FROM debian:buster-slim
+FROM debian:bookworm-slim
 LABEL maintainer="Jamie Curnow <jc@jc21.com>"
 
 SHELL ["/bin/bash", "-o", "pipefail", "-c"]
 
 ARG TARGETPLATFORM
-RUN echo "Base: debian:buster-slim, ${TARGETPLATFORM:-linux/amd64}" > /built-for-arch
+RUN echo "Base: debian:bookworm-slim, ${TARGETPLATFORM:-linux/amd64}" > /built-for-arch
 
 # OpenResty uses LuaJIT which has a dependency on GCC
 RUN apt-get update \
@@ -51,7 +51,7 @@ RUN apt-get update \
 	jq \
 	libncurses6 \
 	libpcre3 \
-	libreadline7 \
+	libreadline8 \
 	openssl \
 	perl \
 	tzdata \
diff --git a/docker/Dockerfile.certbot b/docker/Dockerfile.certbot
index 07454d5..62c6dd9 100644
--- a/docker/Dockerfile.certbot
+++ b/docker/Dockerfile.certbot
@@ -2,7 +2,7 @@
 # Certbot Builder
 #############
 
-FROM debian:buster-slim as certbotbuilder
+FROM debian:bookworm-slim as certbotbuilder
 
 SHELL ["/bin/bash", "-o", "pipefail", "-c"]