Thanks again for the help on this.

I double verified the machine credential is a domain admin, and verified 
that time is in-sync between the ansible tower host and the domain.

I'll try setting ansible_winrm_transport: kerberos and 
ansible_winrm_message_encryption: always and see what happens

On Sunday, March 1, 2020 at 2:31:12 PM UTC-8, Jordan Borean wrote:
>
> The fact that you were able to get a Kerberos ticket showed that your host 
> is set up to get the tickets correctly. Some things you should check
>
>    - The domain account is a local admin, non admins can technically 
>    connect through WinRM but not by default. In any case Ansible is very 
>    limited with what it can do when connecting as a non-admin account so it's 
>    not something we usually document
>    - The time is synced between your Ansible controller and the Windows 
>    server
>    - You aren't using message encryption. This should be done 
>    automatically but some older libraries that Ansible uses may not have it 
>    available. To check set 'ansible_winrm_message_encryption: always' just to 
>    double check message encryption is available and works
>    
>
> Also you should set `ansible_winrm_transport: kerberos' to stop the 
> fallback to Basic auth. Unfortunately this is also another backwards 
> compatibility issue which we can't take away but isn't something that is 
> really optimal.
>

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