Here is a list of 9 items to check.  You may already have done all of these 
but skipping any one of them will prevent it from working.

https://groups.google.com/forum/?utm_medium=email&utm_source=footer#!topic/ansible-project/HKgh7jtsFsk

On Thursday, June 23, 2016 at 9:32:51 AM UTC-5, František Griga wrote:
>
> Hello, 
>
> I have a problem with using Ansible to manage Windows machines. 
>
> I have one virtual machine with Debian 8, Ansible 2.1.0.0 installed 
> through PPA and Python 2.7.9. Then I have a second VM with Windows 10. I 
> would like to send commands from Debian (Ansible) machine to Windows 
> machine using WinRM through HTTPS (I do not want to use Kerberos - I 
> need to connect to Windows local account), but something goes wrong. If 
> I use "ansible_winrm_server_cert_validation: ignore" conf option, 
> everything is fine - I have this: 
>
> root@debx-test:~# ansible 192.168.0.1 -m win_ping 
> 192.168.0.1 | SUCCESS => { 
>      "changed": false, 
>      "ping": "pong" 
> } 
>
> but that is something I do not want to use, because I considere that as 
> a security risk. When I turn the option off, I have this: 
>
> root@debx-test:~# ansible 192.168.0.1 -m win_ping -vvvvv 
> Using /etc/ansible/ansible.cfg as config file 
> Loaded callback minimal of type stdout, v2.0 
> <192.168.0.1> ESTABLISH WINRM CONNECTION FOR USER: admin on PORT 5986 TO 
> 192.168.0.1 
> <192.168.0.1> WINRM CONNECT: transport=plaintext 
> endpoint=https://192.168.0.1:5986/wsman 
> <192.168.0.1> WINRM CONNECTION ERROR: ("bad handshake: Error([('SSL 
> routines', 'SSL3_GET_SERVER_CERTIFICATE', 'certificate verify 
> failed')],)",) 
> Traceback (most recent call last): 
>    File 
> "/usr/lib/python2.7/dist-packages/ansible/plugins/connection/winrm.py", 
> line 152, in _winrm_connect 
>      self.shell_id = protocol.open_shell(codepage=65001) # UTF-8 
>    File "/usr/local/lib/python2.7/dist-packages/winrm/protocol.py", line 
> 132, in open_shell 
>      res = self.send_message(xmltodict.unparse(req)) 
>    File "/usr/local/lib/python2.7/dist-packages/winrm/protocol.py", line 
> 207, in send_message 
>      return self.transport.send_message(message) 
>    File "/usr/local/lib/python2.7/dist-packages/winrm/transport.py", 
> line 173, in send_message 
>      response = self.session.send(prepared_request, 
> timeout=self.read_timeout_sec) 
>    File "/usr/local/lib/python2.7/dist-packages/requests/sessions.py", 
> line 585, in send 
>      r = adapter.send(request, **kwargs) 
>    File "/usr/local/lib/python2.7/dist-packages/requests/adapters.py", 
> line 477, in send 
>      raise SSLError(e, request=request) 
> SSLError: ("bad handshake: Error([('SSL routines', 
> 'SSL3_GET_SERVER_CERTIFICATE', 'certificate verify failed')],)",) 
>
> 192.168.0.1 | UNREACHABLE! => { 
>      "changed": false, 
>      "msg": "plaintext: (\"bad handshake: Error([('SSL routines', 
> 'SSL3_GET_SERVER_CERTIFICATE', 'certificate verify failed')],)\",)", 
>      "unreachable": true 
> } 
>
> does not matter, what certificate I am using. I tried to create CA on 
> Ansible machine, sign Windows CSR, import certificate to Windows, 
> reconfigure HTTPS listener and import CA certificate to trusted 
> certificates on Debian - does not help. I am sure I did everything OK, 
> because it is working for example on the test web server on Windows 
> machine. 
>
> Is it possible to run Ansible with Windows really securelly? How? What 
> should I try? 
>
> Thanks for reply, 
> Frantisek Griga 
>
>

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