- hosts: localhost
  gather_facts: false
  tasks:
    - debug: msg={{item}}
      with_dict: '{{myundef}}'
      when:
       - myundef is defined
      register: shouldskip

    - name: check if skipped
      assert:
        that:
          - shouldskip is skipped

    - debug: msg={{item}}
      loop: '{{myundef|dict2items}}'
      when:
       - myundef is defined

    - debug: msg={{item}}
      with_dict: '{{myundef}}'
      register: notskipped
      ignore_errors: true

    - name: check it failed
      assert:
        that:
          - notskipped is not skipped
          - notskipped is failed
