diff --git a/Dockerfile.openpilot b/Dockerfile.openpilot
index 865f6bdc20..e90eb47a24 100644
--- a/Dockerfile.openpilot
+++ b/Dockerfile.openpilot
@@ -53,6 +53,7 @@ COPY Pipfile Pipfile.lock /tmp/
 RUN pyenv install 3.8.2 && \
     pyenv global 3.8.2 && \
     pyenv rehash && \
+    pip install --no-cache-dir --upgrade pip==20.1.1 && \
     pip install --no-cache-dir pipenv==2018.11.26 && \
     cd /tmp && \
     pipenv install --system --deploy --clear && \
diff --git a/update_requirements.sh b/update_requirements.sh
index 2c9175ecdd..d1fdfd4633 100755
--- a/update_requirements.sh
+++ b/update_requirements.sh
@@ -3,4 +3,4 @@
 DIR="$( cd "$( dirname "${BASH_SOURCE[0]}" )" >/dev/null && pwd )"
 
 cd "$DIR"
-sudo -- bash -c "source /etc/profile.d/comma_dev.sh; pip install pip==19.2.3 git+git://github.com/pypa/pipenv.git@7a12dbb5cacc71d1dd2d74d8cce8eb50ce2db121; pipenv install --dev --deploy --system"
+sudo -- bash -c "source /etc/profile.d/comma_dev.sh; pip install pip==20.1.1 git+git://github.com/pypa/pipenv.git@7a12dbb5cacc71d1dd2d74d8cce8eb50ce2db121; pipenv install --dev --deploy --system"