diff --git a/.github/workflows/e2e.yml b/.github/workflows/e2e.yml
index c4362d36ed..0127bfd66d 100644
--- a/.github/workflows/e2e.yml
+++ b/.github/workflows/e2e.yml
@@ -26,7 +26,7 @@ jobs:
           - connhelper-ssh
         base:
           - alpine
-          - bullseye
+          - bookworm
         engine-version:
 #          - 20.10-dind # FIXME: Fails on 20.10
           - stable-dind # TODO: Use 20.10-dind, stable-dind is deprecated
diff --git a/Dockerfile b/Dockerfile
index c1d3082da2..8b761200a5 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -22,22 +22,15 @@ ARG TARGETPLATFORM
 # gcc is installed for libgcc only
 RUN xx-apk add --no-cache musl-dev gcc
 
-FROM --platform=$BUILDPLATFORM golang:${GO_VERSION}-bullseye AS build-base-bullseye
+FROM --platform=$BUILDPLATFORM golang:${GO_VERSION}-bookworm AS build-base-bookworm
 ENV GOTOOLCHAIN=local
 COPY --link --from=xx / /
 RUN apt-get update && apt-get install --no-install-recommends -y bash clang lld llvm file
 WORKDIR /go/src/github.com/docker/cli
 
-FROM build-base-bullseye AS build-bullseye
+FROM build-base-bookworm AS build-bookworm
 ARG TARGETPLATFORM
-RUN xx-apt-get install --no-install-recommends -y libc6-dev libgcc-10-dev
-# workaround for issue with llvm 11 for darwin/amd64 platform:
-#  # github.com/docker/cli/cmd/docker
-#  /usr/local/go/pkg/tool/linux_amd64/link: /usr/local/go/pkg/tool/linux_amd64/link: running strip failed: exit status 1
-#  llvm-strip: error: unsupported load command (cmd=0x5)
-# more info: https://github.com/docker/cli/pull/3717
-# FIXME: remove once llvm 12 available on debian
-RUN [ "$TARGETPLATFORM" != "darwin/amd64" ] || ln -sfnT /bin/true /usr/bin/llvm-strip
+RUN xx-apt-get install --no-install-recommends -y libc6-dev libgcc-12-dev pkgconf
 
 FROM build-base-${BASE_VARIANT} AS goversioninfo
 ARG GOVERSIONINFO_VERSION
@@ -66,8 +59,6 @@ ARG VERSION
 # PACKAGER_NAME sets the company that produced the windows binary
 ARG PACKAGER_NAME
 COPY --link --from=goversioninfo /out/goversioninfo /usr/bin/goversioninfo
-# in bullseye arm64 target does not link with lld so configure it to use ld instead
-RUN [ ! -f /etc/alpine-release ] && xx-info is-cross && [ "$(xx-info arch)" = "arm64" ] && XX_CC_PREFER_LINKER=ld xx-clang --setup-target-triple || true
 RUN --mount=type=bind,target=.,ro \
     --mount=type=cache,target=/root/.cache \
     --mount=from=dockercore/golang-cross:xx-sdk-extras,target=/xx-sdk,src=/xx-sdk \
@@ -103,7 +94,7 @@ RUN --mount=ro --mount=type=cache,target=/root/.cache \
 FROM build-base-alpine AS e2e-base-alpine
 RUN apk add --no-cache build-base curl openssl openssh-client
 
-FROM build-base-bullseye AS e2e-base-bullseye
+FROM build-base-bookworm AS e2e-base-bookworm
 RUN apt-get update && apt-get install -y build-essential curl openssl openssh-client
 
 FROM docker/buildx-bin:${BUILDX_VERSION}   AS buildx
diff --git a/docker-bake.hcl b/docker-bake.hcl
index 21c3687201..18190ecc89 100644
--- a/docker-bake.hcl
+++ b/docker-bake.hcl
@@ -52,7 +52,7 @@ target "binary" {
     platforms = ["local"]
     output = ["build"]
     args = {
-        BASE_VARIANT = USE_GLIBC == "1" ? "bullseye" : "alpine"
+        BASE_VARIANT = USE_GLIBC == "1" ? "bookworm" : "alpine"
         VERSION = VERSION
         PACKAGER_NAME = PACKAGER_NAME
         GO_STRIP = STRIP_TARGET
@@ -72,7 +72,7 @@ target "plugins" {
     platforms = ["local"]
     output = ["build"]
     args = {
-        BASE_VARIANT = USE_GLIBC == "1" ? "bullseye" : "alpine"
+        BASE_VARIANT = USE_GLIBC == "1" ? "bookworm" : "alpine"
         VERSION = VERSION
         GO_STRIP = STRIP_TARGET
     }
@@ -155,7 +155,7 @@ target "e2e-image" {
     output = ["type=docker"]
     tags = ["${IMAGE_NAME}"]
     args = {
-        BASE_VARIANT = USE_GLIBC == "1" ? "bullseye" : "alpine"
+        BASE_VARIANT = USE_GLIBC == "1" ? "bookworm" : "alpine"
         VERSION = VERSION
     }
 }