Ansible, and openssh on Windows 10

[John Harmon]

Just messing around, but I setup openssh on Windows 10.  My administrative user, john, is configured with the public key for my root user from the ansible server.  I can ssh from ansible to windows 10 without a password, and things look fine.  When trying a simple playbook, however, I get failures left and right.  Just wondering if doing this via ssh is even possible yet with windows?  I see people out there doing this via cygwin, but not necessarily the openssh that ships with Windows 10.

fatal: [win10]: UNREACHABLE! => {"changed": false, "msg": "SSH Error: data could not be sent to remote host \"win10\". Make sure this host can be reached over ssh", "unreachable": true}

[John Harmon]

I am assuming it isn't quite baked yet.  The ControlPath and other things look to be all linux-based (ie. /bin/sh).

TASK [Gathering Facts] *******************************************************************************************************************************************************************************************************************
task path: /etc/ansible/playbooks/one-offs/windows/test.yml:3
<win10> Attempting python interpreter discovery
<win10> ESTABLISH SSH CONNECTION FOR USER: john
<win10> SSH: EXEC ssh -C -o ControlMaster=auto -o ControlPersist=60s -o StrictHostKeyChecking=no -o KbdInteractiveAuthentication=no -o PreferredAuthentications=gssapi-with-mic,gssapi-keyex,hostbased,publickey -o PasswordAuthentication=no -o 'User="john"' -o ConnectTimeout=10 -o ControlPath=/root/.ansible/cp/a2a184ae5b win10 '/bin/sh -c '"'"'echo PLATFORM; uname; echo FOUND; command -v '"'"'"'"'"'"'"'"'/usr/bin/python'"'"'"'"'"'"'"'"'; command -v '"'"'"'"'"'"'"'"'python3.7'"'"'"'"'"'"'"'"'; command -v '"'"'"'"'"'"'"'"'python3.6'"'"'"'"'"'"'"'"'; command -v '"'"'"'"'"'"'"'"'python3.5'"'"'"'"'"'"'"'"'; command -v '"'"'"'"'"'"'"'"'python2.7'"'"'"'"'"'"'"'"'; command -v '"'"'"'"'"'"'"'"'python2.6'"'"'"'"'"'"'"'"'; command -v '"'"'"'"'"'"'"'"'/usr/libexec/platform-python'"'"'"'"'"'"'"'"'; command -v '"'"'"'"'"'"'"'"'/usr/bin/python3'"'"'"'"'"'"'"'"'; command -v '"'"'"'"'"'"'"'"'python'"'"'"'"'"'"'"'"'; echo ENDFOUND && sleep 0'"'"''
<win10> (1, '', 'The system cannot find the path specified.\r\n')
<win10> Failed to connect to the host via ssh: The system cannot find the path specified.
 [WARNING]: Unhandled error in Python interpreter discovery for host win10: unexpected output from Python interpreter discovery

<win10> Interpreter discovery remote stderr:
The system cannot find the path specified.

Using module file /usr/lib/python2.7/site-packages/ansible/modules/system/setup.py
Pipelining is enabled.
<win10> ESTABLISH SSH CONNECTION FOR USER: john
<win10> SSH: EXEC ssh -C -o ControlMaster=auto -o ControlPersist=60s -o StrictHostKeyChecking=no -o KbdInteractiveAuthentication=no -o PreferredAuthentications=gssapi-with-mic,gssapi-keyex,hostbased,publickey -o PasswordAuthentication=no -o 'User="john"' -o ConnectTimeout=10 -o ControlPath=/root/.ansible/cp/a2a184ae5b win10 '/bin/sh -c '"'"'sudo -H -S -n  -u john /bin/sh -c '"'"'"'"'"'"'"'"'echo BECOME-SUCCESS-wwkxsloatrpecpvtnxmjliczqzkrfzle ; /usr/bin/python'"'"'"'"'"'"'"'"' && sleep 0'"'"''
<win10> (1, '', 'The system cannot find the path specified.\r\n')
<win10> Failed to connect to the host via ssh: The system cannot find the path specified.
fatal: [win10]: FAILED! => {
    "ansible_facts": {},
    "changed": false,
    "msg": "The following modules failed to execute: setup\n  setup: MODULE FAILURE\nSee stdout/stderr for the exact error\n"
}

[Richard Bywater]

Haven't used it myself as I only manage Linux hosts but https://docs.ansible.com/ansible/latest/user_guide/windows_faq.html#can-i-connect-to-windows-hosts-over-ssh is relevant to your query.

Richard.

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