Upgrade pip

.circleci/config.yml

@@ -25,6 +25,14 @@ commands:
                 command: |
                     apt-get update --yes && apt-get install --yes python3 python3-venv git make
 
+    upgrade_pip:
+        description: Upgrade the pip version to 20.0.*
+        steps:
+            - run:
+                name: upgrade pip
+                command: |
+                    python3 -m pip install -U pip==20.0.*
+
     build_systemd_image:
         steps:
             - run:
@@ -116,6 +124,9 @@ jobs:
                     - v1-dependencies-py3.6-
 
             - setup_venv
+
+            - upgrade_pip
+
             - run:
                 name: install dependencies
                 command: |
@@ -211,6 +222,7 @@ jobs:
                 key: v1-dependencies-py3.6-sphinx
 
             - setup_venv
+
             - run:
                 name: install dependencies
                 command: |

bootstrap/bootstrap.py

@@ -153,6 +153,15 @@ def main():
         'git+https://github.com/jupyterhub/the-littlest-jupyterhub.git'
     )
 
+    # Upgrade pip
+    run_subprocess([
+        os.path.join(hub_prefix, 'bin', 'pip'),
+        'install',
+        '--upgrade',
+        'pip==20.0.*'
+    ])
+    logger.info('Upgraded pip')
+
     run_subprocess([
         os.path.join(hub_prefix, 'bin', 'pip'),
         'install'