Thanks for this.

Since ansible and pywinrm are behaving the same, it occurs to me that the winrm 
configuration might not suit pywinrm. 

>From the above it appears you have created specific configuration for winrm, 
>rather than using the settings that are applied if you run the 
>ConfigureRemotingForAnsible.ps1.

I suggest you run the  ConfigureRemotingForAnsible.ps1 script on a windows host 
and then compare the winrm configuration with your test machine.

You can see the winrm config by running

Winrm get winrm/config

>From memory, pywinrm can not use credssp authorisation, 

Is your test user a member of the WinRMRemoteWMIUsers__ group? I wouldn't 
expect anything to work if not but just trying to understand what you have in 
place. 

Hope this helps, 

Jon 

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