diff --git a/tools/internal_ci/linux/grpc_xds_bazel_python_test_in_docker.sh b/tools/internal_ci/linux/grpc_xds_bazel_python_test_in_docker.sh
index 8a1a200b249..6ed8856bf0d 100755
--- a/tools/internal_ci/linux/grpc_xds_bazel_python_test_in_docker.sh
+++ b/tools/internal_ci/linux/grpc_xds_bazel_python_test_in_docker.sh
@@ -25,6 +25,7 @@ cd /var/local/git/grpc
 VIRTUAL_ENV=$(mktemp -d)
 virtualenv "$VIRTUAL_ENV"
 PYTHON="$VIRTUAL_ENV"/bin/python
+"$PYTHON" -m pip install --upgrade pip
 "$PYTHON" -m pip install --upgrade grpcio-tools google-api-python-client google-auth-httplib2 oauth2client
 
 # Prepare generated Python code.
diff --git a/tools/internal_ci/linux/grpc_xds_bazel_test_in_docker.sh b/tools/internal_ci/linux/grpc_xds_bazel_test_in_docker.sh
index 03587d76a0c..d0a1338817b 100755
--- a/tools/internal_ci/linux/grpc_xds_bazel_test_in_docker.sh
+++ b/tools/internal_ci/linux/grpc_xds_bazel_test_in_docker.sh
@@ -25,6 +25,7 @@ cd /var/local/git/grpc
 VIRTUAL_ENV=$(mktemp -d)
 virtualenv "$VIRTUAL_ENV"
 PYTHON="$VIRTUAL_ENV"/bin/python
+"$PYTHON" -m pip install --upgrade pip
 "$PYTHON" -m pip install --upgrade grpcio grpcio-tools google-api-python-client google-auth-httplib2 oauth2client
 
 # Prepare generated Python code.
diff --git a/tools/run_tests/helper_scripts/prep_xds.sh b/tools/run_tests/helper_scripts/prep_xds.sh
index 9c3a67386ea..ab15e2eb1c8 100755
--- a/tools/run_tests/helper_scripts/prep_xds.sh
+++ b/tools/run_tests/helper_scripts/prep_xds.sh
@@ -19,6 +19,7 @@ set -ex
 cd "$(dirname "$0")/../../.."
 
 sudo apt-get install -y python3-pip
+sudo python3 -m pip install --upgrade pip
 sudo python3 -m pip install grpcio grpcio-tools google-api-python-client google-auth-httplib2 oauth2client
 
 # Prepare generated Python code.