So just sharing the solution presented below by Slim Slam, also works on 
Fedora 23. Again, I understand it is not an ideal solution but if you are 
tied on any Ansible version < 2 and can't upgrade, it works as a temporally 
solution or workaround.

On Sunday, October 11, 2015 at 1:21:05 AM UTC-4, Slim Slam wrote:
>
>
> Using Ansible 1.9.4 and Python 2.7.10 on MacOSX 10.10.5
>
> When attempting:
>
> env ANSIBLE_LOAD_CALLBACK_PLUGINS=1 ansible winserv -i ../windows_servers 
> -m win_ping
>
> I get:
>
> 54.68.166.123 | FAILED => 500 WinRMTransport. [SSL: 
> CERTIFICATE_VERIFY_FAILED] certificate verify failed (_ssl.c:590)
>
> As suggested in previous postings, I have a file named fix-ssl.py in my 
> callback_plugins folder:
>
> import ssl
> if hasattr(ssl, '_create_default_https_context') and hasattr(ssl, 
> '_create_unverified_context'):
>     ssl._create_default_https_context = ssl._create_unverified_context
>
> class CallbackModule(object):
>     pass
>
> And in my ansible.cfg file, I have:
>
> bin_ansible_callbacks=True
> callback_plugins = /callback_plugins/fix-ssl.py
>
> How can I get this to work?
>
>

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