diff --git a/Dockerfile b/Dockerfile
index 49303f4d206..d38fef99173 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -71,7 +71,7 @@ RUN sed -i 's/\r$//' docker/install_auto_router.sh && chmod +x docker/install_au
 
 # Force patched jaraco.context version (GHSA-58pv-8j8x-9vj2)
 # Must be after install_auto_router.sh as aurelio-sdk may downgrade jaraco.context
-RUN pip install --no-cache-dir 'jaraco.context>=6.1.0'
+RUN pip install --no-cache-dir --upgrade 'jaraco.context>=6.1.0'
 
 # Generate prisma client
 RUN prisma generate
diff --git a/docker/Dockerfile.database b/docker/Dockerfile.database
index 605d5eccbc0..645fa410634 100644
--- a/docker/Dockerfile.database
+++ b/docker/Dockerfile.database
@@ -69,7 +69,7 @@ RUN sed -i 's/\r$//' docker/install_auto_router.sh && chmod +x docker/install_au
 
 # Force patched jaraco.context version (GHSA-58pv-8j8x-9vj2)
 # Must be after install_auto_router.sh as aurelio-sdk may downgrade jaraco.context
-RUN pip install --no-cache-dir 'jaraco.context>=6.1.0'
+RUN pip install --no-cache-dir --upgrade 'jaraco.context>=6.1.0'
 
 # ensure pyjwt is used, not jwt
 RUN pip uninstall jwt -y