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

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