diff --git a/jobs/templates/swh-cypress.groovy b/jobs/templates/swh-cypress.groovy
--- a/jobs/templates/swh-cypress.groovy
+++ b/jobs/templates/swh-cypress.groovy
@@ -46,6 +46,7 @@
         sh '''#!/bin/bash
         python3 -m venv ~/swh-web-env
         source ~/swh-web-env/bin/activate
+        pip3 install --upgrade pip
         pip3 install wheel
         pip3 install -e .[testing]
         yarn install && yarn build-test && yarn run cypress install
diff --git a/jobs/templates/swh-cypress.yaml b/jobs/templates/swh-cypress.yaml
--- a/jobs/templates/swh-cypress.yaml
+++ b/jobs/templates/swh-cypress.yaml
@@ -63,6 +63,7 @@
           set -e
           python3 -m venv ~/swh-web-env
           source ~/swh-web-env/bin/activate
+          pip3 install --upgrade pip
           pip3 install wheel
           pip3 install -e .[testing]
           yarn install && yarn build-test && yarn run cypress install