For testing locally I'm assuming you mean Test-WSMan -Authentication Basic 
-Credential <problem account> ? I am currently connecting on 5986 with 
ignore certificate validation turned on.
So in that case I would add -UseSSL switch on the Test-WSMan. Currently 
running Test-WSMan -Authentication Basic -Credential <problem account> 
gives:

Test-WSMAN : <f:WSManFault 
xmlns:f="http://schemas.microsoft.com/wbem/wsman/1/wsmanfault"; 
Code="2150858974" Machine="Server101"><f:Message>The WinRM client cannot 
process the request. Unencrypted traffic is currently disabled in the 
client configuration. Change the client configuration and try the request 
again. </f:Message></f:WSManFault>
At line:1 char:1

Normally I would say that would mean mean configuring AllowUnencrypted on 
Winrm Client, however the other working systems do not have this configured.

Running Test-WSMAN -Authentication Negotiate -Credential "<user>" 
-ComputerName localhost returns:

wsmid           : 
http://schemas.dmtf.org/wbem/wsman/identity/1/wsmanidentity.xsd
ProtocolVersion : http://schemas.dmtf.org/wbem/wsman/1/wsman.xsd
ProductVendor   : Microsoft Corporation
ProductVersion  : OS: 6.3.9600 SP: 0.0 Stack: 3.0

I will try the Fiddler method shortly and return the results.

On Friday, May 27, 2016 at 7:48:53 PM UTC+2, Matt Davis wrote:
>
> Hey Mike,
>
> Unfortunately pywinrm currently has *zero* logging/diagnostic capabilities 
> (something I'd like to correct for troubleshooting stuff like this). 
> Meantime...
>
> A couple of things to try:
> - Does it work with Basic auth and a local user on that same box?
> - Any chance you could run with Fiddler in the middle? Just run Fiddler on 
> some Windows box, configure it to capture/decrypt HTTPS and to allow 
> external connection, then on your Ansible controller, export 
> HTTPS_PROXY=http://(ip-of-fiddler-box):8888/ and go watch the fun.
>
> I'm mostly just curious where the connection reset is occurring, as there 
> are numerous round-trips involved here (eg, is it NTLM auth failure, 
> resource issue, or something else?).
>
> Thanks,
>
> -Matt
>
>
> On Friday, May 27, 2016 at 7:26:32 AM UTC-7, Mike Fennemore wrote:
>>
>> I have a selected few workgroup Windows server 2012 R2 servers that give 
>> the following error:
>>
>> <10.128.44.37> ESTABLISH WINRM CONNECTION FOR USER: ansible_user on PORT 
>> 5986 TO 10.128.44.37
>> server_101 | UNREACHABLE! => {
>>     "changed": false,
>>     "msg": "ntlm: ('Connection aborted.', error(104, 'Connection reset by 
>> peer'))",
>>     "unreachable": true
>> }
>>
>> I am using ntlm with Ansible 2.1.0.0 and pywinrm [kerberos] 2RC4. I have 
>> tested the port is open, recreated the listeners, run a curl to the server 
>> which delivers a successful 411 response.
>> Any ideas on further troubleshooting?
>>
>>
>>

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