diff --git a/roles/wsgi_website/tasks/main.yml b/roles/wsgi_website/tasks/main.yml
index 5f194c3103968976401cc9b22b36daa0f917b69a..e20812dc5310950d213c7d828aa117c0e9f638cb 100644
--- a/roles/wsgi_website/tasks/main.yml
+++ b/roles/wsgi_website/tasks/main.yml
@@ -122,6 +122,27 @@
     #   created (thanks to 'creates' parameter).
     - skip_ansible_lint
 
+- name: Install latest pip in virtual environment
+  pip:
+    name:
+      - "pip>=18.0.0,<19.0.0"
+    virtualenv: "{{ home }}/virtualenv"
+  become: true
+  become_user: "{{ admin }}"
+
+# Workaround for:
+#
+# - https://github.com/pypa/pip/issues/4022
+# - https://bugs.launchpad.net/ubuntu/+source/python-pip/+bug/1635463
+# - https://bugs.debian.org/cgi-bin/bugreport.cgi?bug=871790
+- name: Remove the pkg-resources package from virtual environment (see comments above for details)
+  pip:
+    name: pkg-resources
+    virtualenv: "{{ home }}/virtualenv"
+    state: absent
+  become: true
+  become_user: "{{ admin }}"
+
 - name: Configure project directory for the Python virtual environment
   template:
     src: "venv_project.j2"