Hey There is a myriad of reasons why this might not work but here is where I would start. Run the following commands in Powershell and paste the info here and we should be able to help a bit more
Write-Host "WinRM Service Settings" winrm get winrm/config/service Write-Host "WinRM Listener Info" winrm enumerate winrm/config/Listener $listener = Get-WSManInstance -ResourceURI 'winrm/config/Listener' - SelectorSet @{ Transport = "HTTPS"; Address = "*" } if ($listener) { $thumbprint = $listener.CertificateThumbprint $certificate = Get-ChildItem -Path Cert:\LocalMachine\My | Where-Object { $_.Thumbprint -eq $thumbprint } if ($certificate) { Write-Host "Certificate Metadata" Write-Host "Signature Algorithm: $($certificate.SignatureAlgorithm.FriendlyName)" Write-Host "Valid To: $($certificate.NotAfter.DateTime)" } else { Write-Host "Unable to find certificate info for thumbprint: $thumbprint" } } Other things that would be good to know if the version of your pywinrm and dependencies, are you able to run the below and tell us the version of pywinrm, requests-ntlm and ntlm-auth. pip list You can also try and just connecting to your Windows Server directly with Powershell to try and rule out whether it is pywinrm or some host configuration. Thanks Jordan -- You received this message because you are subscribed to the Google Groups "Ansible Project" group. To unsubscribe from this group and stop receiving emails from it, send an email to ansible-project+unsubscr...@googlegroups.com. To post to this group, send email to ansible-project@googlegroups.com. To view this discussion on the web visit https://groups.google.com/d/msgid/ansible-project/c168b48f-f926-48fb-bb7d-e679cf9f2a45%40googlegroups.com. For more options, visit https://groups.google.com/d/optout.