--- - name: Find all EXTERNALLY-MANAGED files under /usr/lib/python* find: paths: /usr/lib patterns: "EXTERNALLY-MANAGED" file_type: file recurse: yes register: externally_managed_files become: yes - name: Delete EXTERNALLY-MANAGED files file: path: "{{ item.path }}" state: absent loop: "{{ externally_managed_files.files }}" when: externally_managed_files.matched > 0 become: yes