You should consider upgrading via the 'pip install --upgrade pip' command. $ echo $PATH /home/gitlab-runner/builds/DPfEafLZ/0/sbilal/pythonapp/python3-virtualenv/bin:/usr/local/sbin:/usr/local/bin:/usr/sbin:/usr/bin $ if [[ $CI_COMMIT_REF_NAME = master ]]; then # collapsed multi-line command deploying to prod server Failed to start python.service: Interactive authentication required. See system logs and 'systemctl status python.service' for details. Cleaning up project directory and file based variables ERROR: Job failed: exit status 1