diff --git a/.gitignore b/.gitignore
index 4c0fc20..64b7b65 100644
--- a/.gitignore
+++ b/.gitignore
@@ -8,3 +8,4 @@ Dockerfile
 web-wasm/Dockerfile
 */imagefiles/*
 !imagefiles/*
+crosstool-ng/*
diff --git a/Dockerfile.in b/Dockerfile.in
index c9b082c..ce697cb 100644
--- a/Dockerfile.in
+++ b/Dockerfile.in
@@ -1,4 +1,4 @@
-ARG DOCKER_IMAGE=debian:bullseye-slim
+ARG DOCKER_IMAGE=debian:bookworm-slim
 FROM $DOCKER_IMAGE
 
 LABEL maintainer="Matt McCormick matt.mccormick@kitware.com"
diff --git a/imagefiles/install-python-packages.sh b/imagefiles/install-python-packages.sh
index 964e5ed..2356015 100755
--- a/imagefiles/install-python-packages.sh
+++ b/imagefiles/install-python-packages.sh
@@ -23,10 +23,11 @@ cd /tmp
 curl -# -LO https://bootstrap.pypa.io/pip/get-pip.py
 # https://github.com/pypa/setuptools/issues/2993
 export SETUPTOOLS_USE_DISTUTILS=stdlib
-${PYTHON} get-pip.py --ignore-installed
+# Add --break-system-packages to fix change since python 3.11: https://stackoverflow.com/a/75722775/10152334
+${PYTHON} get-pip.py --ignore-installed --break-system-packages 
 rm get-pip.py
 
-${PYTHON} -m pip install --upgrade --ignore-installed setuptools
-${PYTHON} -m pip install --ignore-installed conan meson
+${PYTHON} -m pip install --break-system-packages --upgrade --ignore-installed setuptools
+${PYTHON} -m pip install --break-system-packages --ignore-installed conan meson
 # Purge cache to save space: https://stackoverflow.com/questions/37513597/is-it-safe-to-delete-cache-pip-directory
 ${PYTHON} -m pip cache purge