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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