--- - name: certbot | PyPI | Upgrade pip, setuptools, and pyopenssl as required pip: name: "{{ item }}" executable: "{{ certbot_pip_executable }}" loop: - pip - setuptools - pyopenssl - name: certbot | PyPI | Install certbot {{ certbot_pip_version }} pip: name: certbot=={{ certbot_pip_version }} executable: "{{ certbot_pip_executable }}" - name: certbot | PyPI | Install certbot plugins pip: name: "certbot-{{ item }}=={{ certbot_pip_version }}" executable: "{{ certbot_pip_executable }}" loop: "{{ certbot_plugins }}" when: certbot_plugins is defined