diff --git a/docker/python-base/Dockerfile b/docker/python-base/Dockerfile
index 762407dddb..15ec96fc1a 100644
--- a/docker/python-base/Dockerfile
+++ b/docker/python-base/Dockerfile
@@ -19,5 +19,10 @@ RUN apt-get update \
   && apt-get install -y dumb-init libjemalloc2 \
   && apt-get clean \
   && rm -rf /var/lib/apt/lists/*
+
+# Upgrade pip to fix wheel cache for locally built wheels
+# See https://github.com/pypa/pip/issues/6852
+RUN pip install -U pip
+
 ENV LD_PRELOAD /usr/lib/x86_64-linux-gnu/libjemalloc.so.2
 ENTRYPOINT ["/usr/bin/dumb-init", "--"]
diff --git a/docker/python-builder/Dockerfile b/docker/python-builder/Dockerfile
index 3e8efbc517..b8e5b5faf9 100644
--- a/docker/python-builder/Dockerfile
+++ b/docker/python-builder/Dockerfile
@@ -32,3 +32,7 @@ RUN dpkg -i /tmp/python3-dev_4.0.0_all.deb \
   && rm /tmp/python3-dev_4.0.0_all.deb \
   && pip install --no-cache-dir bindep \
   && rm -rf /var/lib/apt/lists/*
+
+# Upgrade pip to fix wheel cache for locally built wheels
+# See https://github.com/pypa/pip/issues/6852
+RUN pip install -U pip