I see there is possibility of issue with pywinrm
https://github.com/diyan/pywinrm/issues/201
looks similar

On Wednesday, February 5, 2020 at 2:38:30 PM UTC+5:30, Bhushan Gholave 
wrote:
>
> Hi All,
>
> Issue closed : https://github.com/ansible/ansible/issues/67114
>
> 1. host file 
> [windows]
>
> 192.152.1.21 ansible_user=administrator ansible_password=Password123 
> ansible_port=5986 ansible_winrm_transport=basic 
> ansible_winrm_server_cert_validation=ignore ansible_connection=winrm
>
> 2. run *ansible -i host -m win_ping all - *with ansible version 2.8.5
> response:-
>
> 192.152.1.21 | SUCCESS => {
>     "changed": false,
> }
>     "ping": "pong"
>
> 3. run *ansible -i host -m win_ping all - *with ansible version 2.9.4
> response:- 
>
> 192.152.1.21 | UNREACHABLE! => {
>     "changed": false,
>     "msg": "basic: HTTPSConnectionPool(host='192.152.1.21', port=5986): Max 
> retries exceeded with url: /wsman (Caused by SSLError(SSLError(1, '[SSL: 
> UNSUPPORTED_PROTOCOL] unsupported protocol (_ssl.c:897)'),))",
>     "unreachable": true
> }
>
> 4. I followed 
> https://docs.ansible.com/ansible/latest/user_guide/windows_setup.html 
> documentation to setup windows host. I run Upgrade-PowerShell.ps1, 
>
> Install-WMF3Hotfix.ps1, ConfigureRemotingForAnsible.ps1 and winrm settings 
> mentioned.
>
> 5. Work around if i do *.\ConfigureRemotingForAnsible.ps1 -ForceNewSSLCert* 
> then it start working on both version.
>
> 6. I think even if we give *ansible_winrm_server_cert_validation=ignore* flag 
> still it search for self sign certificate on target machine.
> My guess might be wrong but we need to find out exact reason behind this.
>
> Thanks,
>
> Bhushan
>
>
>

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