I had something like it, not on Windows though,at the time the problem was
that I set it not to gather_facts, when I actually tried to use a few facts
later on. May not be the same but may be worth checking..

Alex

On Thursday, 11 February 2016, Michael Baydoun <[email protected]>
wrote:

> This is still occurring during our full site.yml run, but it's so far
> impossible to replicate in a small example.  It only occurs on our full
> site.yml run with no limits, any attempt to limit to certain hosts or tags
> result in no errors.
>
> On Wednesday, February 3, 2016 at 9:56:26 AM UTC-5, Michael Baydoun wrote:
>>
>> Some ansible playbook runs will work on most hosts, but 1-3 will fail
>> with an undefined variable that is an ansible fact.  Run it a second time
>> and it works.
>> Example:
>>
>> fatal: [wdv-sitefinity1]: FAILED! => {"failed": true, "msg": "ERROR! The
>> conditional check 'ansible_os_family == 'Windows'' failed. The error was:
>> ERROR! error while evaluating conditional (ansible_os_family == 'Windows'):
>> ERROR! 'ansible_os_family' is undefined\n\nThe error appears to have been
>> in '/home/icansible/ansible/roles/newrelic/tasks/main.yml': line 11, column
>> 3, but may\nbe elsewhere in the file depending on the exact syntax
>> problem.\n\nThe offending line appears to be:\n\n\n- name: create temp
>> directory\n  ^ here\n"}
>>
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