included.yml

- name: install monit
  package: name=monit state=present

- name: add monit config
  copy:
  args:
    src: "{{ monitrc }}"
    dest: "/etc/monitrc"
    mode: 0600
  loop_control:
    loop_var: monitrc
  with_first_found:
    - files:
        - "{{ role_path }}/files/{{ os }}.monitrc"
        - "{{ role_path }}/files/{{ os|stripversion }}.monitrc"

output.txt

TASK [jenkins-worker : enable jenkins at startup] ******************************
ok: [test-joyent-smartos15-x64-1]

TASK [jenkins-worker : install monit] ******************************************
skipping: [test-joyent-smartos15-x64-1]

TASK [jenkins-worker : add monit config] ***************************************
 [WARNING]: Unable to find '/Users/jbergstroem/Work/node/build/ansible/roles/jenkins-worker/files/smartos15.monitrc' in expected paths.

 [WARNING]: Unable to find '/Users/jbergstroem/Work/node/build/ansible/roles/jenkins-worker/files/smartos.monitrc' in expected paths.

fatal: [test-joyent-smartos15-x64-1]: FAILED! => {"failed": true, "msg": "No file was found when using with_first_found. Use the 'skip: true' option to allow this task to be skipped if no files are found"}

PLAY RECAP *********************************************************************
test-joyent-smartos15-x64-1 : ok=17   changed=2    unreachable=0    failed=1   

parent.yml

- name: install monit
  when: os in needs_monit
  include: monit.yml