diff --git a/runner/Dockerfile b/runner/Dockerfile
index f7383f02..2797689a 100644
--- a/runner/Dockerfile
+++ b/runner/Dockerfile
@@ -62,6 +62,7 @@ RUN set -vx; \
     && echo "%sudo   ALL=(ALL:ALL) NOPASSWD:ALL" > /etc/sudoers
 
 ENV RUNNER_ASSETS_DIR=/runnertmp
+ENV HOME=/home/runner
 
 # Runner download supports amd64 as x64. Externalstmp is needed for making mount points work inside DinD.
 #
@@ -88,6 +89,9 @@ RUN echo AGENT_TOOLSDIRECTORY=/opt/hostedtoolcache > .env \
 COPY entrypoint.sh /
 COPY --chown=runner:docker patched $RUNNER_ASSETS_DIR/patched
 
+# Add the Python "User Script Directory" to the PATH
+ENV PATH="${PATH}:${HOME}/.local/bin"
+
 USER runner
 ENTRYPOINT ["/usr/local/bin/dumb-init", "--"]
 CMD ["/entrypoint.sh"]
diff --git a/runner/Dockerfile.dindrunner b/runner/Dockerfile.dindrunner
index 25b53ffc..be8a3003 100644
--- a/runner/Dockerfile.dindrunner
+++ b/runner/Dockerfile.dindrunner
@@ -73,6 +73,7 @@ RUN export ARCH=$(echo ${TARGETPLATFORM} | cut -d / -f2) \
 	docker --version
 
 ENV RUNNER_ASSETS_DIR=/runnertmp
+ENV HOME=/home/runner
 
 # Runner download supports amd64 as x64
 #
@@ -110,6 +111,9 @@ VOLUME /var/lib/docker
 
 COPY --chown=runner:docker patched $RUNNER_ASSETS_DIR/patched
 
+# Add the Python "User Script Directory" to the PATH
+ENV PATH="${PATH}:${HOME}/.local/bin"
+
 # No group definition, as that makes it harder to run docker.
 USER runner
 
diff --git a/runner/Dockerfile.ubuntu.1804 b/runner/Dockerfile.ubuntu.1804
index fa62ce4e..8cc53e7c 100644
--- a/runner/Dockerfile.ubuntu.1804
+++ b/runner/Dockerfile.ubuntu.1804
@@ -62,6 +62,7 @@ RUN set -vx; \
     && echo "%sudo   ALL=(ALL:ALL) NOPASSWD:ALL" > /etc/sudoers
 
 ENV RUNNER_ASSETS_DIR=/runnertmp
+ENV HOME=/home/runner
 
 # Runner download supports amd64 as x64. Externalstmp is needed for making mount points work inside DinD.
 #
@@ -88,6 +89,9 @@ RUN echo AGENT_TOOLSDIRECTORY=/opt/hostedtoolcache > .env \
 COPY entrypoint.sh /
 COPY --chown=runner:docker patched $RUNNER_ASSETS_DIR/patched
 
+# Add the Python "User Script Directory" to the PATH
+ENV PATH="${PATH}:${HOME}/.local/bin"
+
 USER runner
 ENTRYPOINT ["/usr/local/bin/dumb-init", "--"]
 CMD ["/entrypoint.sh"]