I've taken to just brute-force running the same playbook over and over 
again until the issue goes away.  I still suspect GPO or replication or 
time... or something

However - one clue - When the kerberos error happens, I see this generated 
in the log files:

 Log Name:      System
Source:        Microsoft-Windows-WinRM
Date:          3/1/2020 6:16:34 PM
Event ID:      10154
Task Category: None
Level:         Warning
Keywords:      Classic
User:          N/A
Computer:      hostname.internal.domain
Description:
The WinRM service failed to create the following SPNs: 
WSMAN/hostname.internal.domain; WSMAN/hostname. 

 Additional Data 
 The error received was 1355: %%1355.

 User Action 
 The SPNs can be created by an administrator using setspn.exe utility.

On Sunday, March 1, 2020 at 2:58:06 PM UTC-8, Dave York wrote:
>
> Second Run (from failure) gets further (?!?!)
>
> [image: ansible-krb3.png]
>
>
>
>
> On Sunday, March 1, 2020 at 2:57:18 PM UTC-8, Dave York wrote:
>>
>> First run looks the same:
>>
>> [image: ansible-krb2.png]
>>
>>
>>
>>
>>
>>
>>
>>
>> On Sunday, March 1, 2020 at 2:38:29 PM UTC-8, Dave York wrote:
>>>
>>> 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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