diff --git a/.azure-pipelines-gh-pages.yml b/.azure-pipelines-gh-pages.yml
index b29674f558d3..daacaf33df08 100644
--- a/.azure-pipelines-gh-pages.yml
+++ b/.azure-pipelines-gh-pages.yml
@@ -56,6 +56,7 @@ jobs:
           set -ex
           python3.8 -m venv env
           source env/bin/activate
+          pip install -U pip
           pip install -U -e ./python
           pip install -U -r doc/requirements.txt
           pip install -U -r doc/historical_ccf_requirements.txt
@@ -72,6 +73,7 @@ jobs:
           set -ex
           python3.8 -m venv env
           source env/bin/activate
+          pip install -U pip
           pip install -U -e ./python
           pip install -U -r doc/requirements.txt
           sphinx-build doc build/html
diff --git a/tests/test_install.sh b/tests/test_install.sh
index d08b5fbab403..a49474cbf1d8 100755
--- a/tests/test_install.sh
+++ b/tests/test_install.sh
@@ -54,6 +54,7 @@ fi
 python3.8 -m venv env
 # shellcheck source=/dev/null
 source env/bin/activate
+python -m pip install -U pip
 python -m pip install -U -e ../../../python
 
 # Poll until service has died