[ansible] Checking for multiple conditions using "when" on single task in ansible

Adding to https://stackoverflow.com/users/1638814/nvartolomei answer, which will probably fix your error.

Strictly answering your question, I just want to point out that the when: statement is probably correct, but would look easier to read in multiline and still fulfill your logic:

when: 
  - sshkey_result.rc == 1
  - github_username is undefined or 
    github_username |lower == 'none'

https://docs.ansible.com/ansible/latest/user_guide/playbooks_conditionals.html#the-when-statement