Thanks Jon, good to see it's being well maintained. Had already gone down 
the route of the self-signed cert via Powershell unfortunately.
I ran the ConfigureForAnsible.ps1 just in case I had missed something. 
Seems like the same issue though:

<xx.xx.xx.xx> ESTABLISH WINRM CONNECTION FOR USER: ansible_user@DOMAIN on 
PORT 5986 TO xx.xx.xx.xx
Server.domain | UNREACHABLE! => {
    "changed": false,
    "msg": "ntlm: ('Connection aborted.', error(104, 'Connection reset by 
peer'))",
    "unreachable": true
}


On Monday, June 6, 2016 at 2:35:39 PM UTC+2, J Hawkesworth wrote:
>
> Interesting. 
>
> This change was recently added so you can force the 
> ConfigureRemotingForAnsible.ps1 to generate a new self-signed cert by 
> running like this:
>
> .\ConfigureRemotingForAnsible.ps1 -ForceNewSSLCert true
>
> https://github.com/ansible/ansible/pull/15275
>
> As its says in the PR 'This is necessary when a CN name changes and the 
> self-signed cert is no longer valid and winRM is not allowing a connection 
> because of winRM SSL validation errors.'
>
> Hope this helps,
>
> Jon
>
> On Monday, June 6, 2016 at 1:20:21 PM UTC+1, Mike Fennemore wrote:
>>
>> I'm beginning to think this might be as a result of the problem servers 
>> being templated in VMWare perhaps?
>>
>> On Wednesday, June 1, 2016 at 7:41:50 PM UTC+2, Matt Davis wrote:
>>>
>>> Sorry, by "local user" I just meant using a non-domain user via 
>>> pywinrm/Ansible. But yeah, for Basic to work, you'd have to (temporarily) 
>>> enable unencrypted auth with something like:
>>>
>>> Set-Item WSMan:\localhost\Service\AllowUnencrypted $true
>>>
>>> The HTTPS_PROXY not working seems odd- I use it dozens of times a day... 
>>> Sure you've got it exported? The problem is almost certainly on the 
>>> control-machine side, as it'd just hang if the envvar worked and Fiddler 
>>> wasn't configured properly.
>>>
>>> On Monday, May 30, 2016 at 12:45:48 AM UTC-7, Mike Fennemore wrote:
>>>>
>>>> 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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