diff --git a/lib/functions/cli/cli-requirements.sh b/lib/functions/cli/cli-requirements.sh
index eafe0546e7..67b8cc3481 100644
--- a/lib/functions/cli/cli-requirements.sh
+++ b/lib/functions/cli/cli-requirements.sh
@@ -22,11 +22,14 @@ function cli_requirements_run() {
 	host_release="${HOSTRELEASE}" host_arch="${HOSTARCH}" early_prepare_host_dependencies
 
 	LOG_SECTION="install_host_dependencies" do_with_logging install_host_dependencies "for requirements command"
+	declare -i -g -r prepare_host_has_already_run=1 # global, readonly. fool the rest of the script into thinking we've already run prepare_host.
 
 	if [[ "${ARMBIAN_INSIDE_DOCKERFILE_BUILD}" == "yes" ]]; then
+		# Include python/pip packages in the Dockerfile build.
+		deploy_to_non_cache_dir="yes" prepare_python_and_pip
+
 		# During the Dockerfile build, we want to pre-download ORAS/shellcheck/shfmt so it's included in the image.
 		# We need to change the deployment directory to something not in ./cache, so it's baked into the image.
-
 		deploy_to_non_cache_dir="yes" run_tool_oras       # download-only, to non-cache dir.
 		deploy_to_non_cache_dir="yes" run_tool_shellcheck # download-only, to non-cache dir.
 
diff --git a/lib/functions/general/python-tools.sh b/lib/functions/general/python-tools.sh
index 0e92933162..0b1d30523f 100644
--- a/lib/functions/general/python-tools.sh
+++ b/lib/functions/general/python-tools.sh
@@ -55,11 +55,24 @@ function prepare_python_and_pip() {
 	early_prepare_pip3_dependencies_for_python_tools
 	python3_pip_dependencies_hash="$(echo "${HOSTRELEASE}" "${python3_version}" "${pip3_version}" "${python3_pip_dependencies[*]}" | sha256sum | cut -d' ' -f1)"
 
+	declare non_cache_dir="/armbian-pip"
 	declare python_pip_cache="${SRC}/cache/pip"
+
+	if [[ "${deploy_to_non_cache_dir:-"no"}" == "yes" ]]; then
+		display_alert "Using non-cache dir" "PIP: ${non_cache_dir}" "warn"
+		python_pip_cache="${non_cache_dir}"
+	else
+		# if the non-cache dir exists, copy it into place, if not already existing...
+		if [[ -d "${non_cache_dir}" && ! -d "${python_pip_cache}" ]]; then
+			display_alert "Deploying pip cache from Docker image" "${non_cache_dir} -> ${python_pip_cache}" "info"
+			run_host_command_logged cp -pr "${non_cache_dir}" "${python_pip_cache}"
+		fi
+	fi
+
 	declare python_hash_base="${python_pip_cache}/pip_pkg_hash"
 	declare python_hash_file="${python_hash_base}_${python3_pip_dependencies_hash}"
-	declare python3_user_base="${SRC}/cache/pip/base"
-	declare python3_pycache="${SRC}/cache/pip/pycache"
+	declare python3_user_base="${python_pip_cache}/base"
+	declare python3_pycache="${python_pip_cache}/pycache"
 
 	# declare a readonly global dict with all needed info for executing stuff using this setup
 	declare -r -g -A PYTHON3_INFO=(
diff --git a/lib/functions/host/docker.sh b/lib/functions/host/docker.sh
index 363daf8d4a..9cad36cb43 100755
--- a/lib/functions/host/docker.sh
+++ b/lib/functions/host/docker.sh
@@ -251,11 +251,19 @@ function docker_cli_prepare_dockerfile() {
 
 	# This includes apt install equivalent to install_host_dependencies()
 	display_alert "Creating" "Dockerfile; FROM ${DOCKER_ARMBIAN_BASE_IMAGE}" "info"
+
 	declare c="" # Nothing; commands will run.
 	if [[ "${DOCKER_SIMULATE_CLEAN}" == "yes" ]]; then
 		display_alert "Simulating" "clean build, due to DOCKER_SIMULATE_CLEAN=yes -- this is wasteful and slow and only for debugging" "warn"
 		c="## " # Add comment to simulate clean env
 	fi
+
+	declare c_req="# " # Nothing; commands will run.
+	if [[ "${DOCKERFILE_USE_ARMBIAN_IMAGE_AS_BASE}" == "no" ]]; then
+		display_alert "Dockerfile build will include tooling/requirements" "due to DOCKERFILE_USE_ARMBIAN_IMAGE_AS_BASE=no" "info"
+		c_req=""
+	fi
+
 	cat <<- INITIAL_DOCKERFILE > "${SRC}"/Dockerfile
 		${c}# PLEASE DO NOT MODIFY THIS FILE. IT IS AUTOGENERATED AND WILL BE OVERWRITTEN. Please don't build this Dockerfile yourself either. Use Armbian ./compile.sh instead.
 		FROM ${DOCKER_ARMBIAN_BASE_IMAGE}
@@ -268,9 +276,9 @@ function docker_cli_prepare_dockerfile() {
 		WORKDIR ${DOCKER_ARMBIAN_TARGET_PATH}
 		ENV ARMBIAN_RUNNING_IN_CONTAINER=yes
 		ADD . ${DOCKER_ARMBIAN_TARGET_PATH}/
-		${c}RUN echo "--> CACHE MISS IN DOCKERFILE: running Armbian requirements initialization." && \\
-		${c} ARMBIAN_INSIDE_DOCKERFILE_BUILD="yes" /bin/bash "${DOCKER_ARMBIAN_TARGET_PATH}/compile.sh" requirements SHOW_LOG=yes && \\
-		${c} rm -rf "${DOCKER_ARMBIAN_TARGET_PATH}/output" "${DOCKER_ARMBIAN_TARGET_PATH}/.tmp" "${DOCKER_ARMBIAN_TARGET_PATH}/cache"
+		${c}${c_req}RUN echo "--> CACHE MISS IN DOCKERFILE: running Armbian requirements initialization." && \\
+		${c}${c_req} ARMBIAN_INSIDE_DOCKERFILE_BUILD="yes" /bin/bash "${DOCKER_ARMBIAN_TARGET_PATH}/compile.sh" requirements SHOW_LOG=yes && \\
+		${c}${c_req} rm -rf "${DOCKER_ARMBIAN_TARGET_PATH}/output" "${DOCKER_ARMBIAN_TARGET_PATH}/.tmp" "${DOCKER_ARMBIAN_TARGET_PATH}/cache"
 		${include_dot_git_dir}
 	INITIAL_DOCKERFILE
 	# For debugging: RUN rm -fv /usr/bin/pip3 # Remove pip3 symlink to make sure we're not depending on it; non-Dockers may not have it