It might also help to add that all the servers it seems to be failing on 
are Windows Server 2012 R2 with IIS installed and a few sites with 
different SSL Certificates installed.

On Friday, June 24, 2016 at 2:48:18 PM UTC+2, Mike Fennemore wrote:
>
> 09:12:58:4855 fiddler.network.https> HTTPS handshake to 10.128.44.38 (for 
> #2) failed. System.ComponentModel.Win32Exception The client and server 
> cannot communicate, because they do not possess a common algorithm
>
>
> 09:13:34:4067 fiddler.network.https> HTTPS handshake to 10.128.44.38 (for 
> #3) failed. System.ComponentModel.Win32Exception The client and server 
> cannot communicate, because they do not possess a common algorithm
>
>
> 09:17:40:7434 fiddler.network.https> HTTPS handshake to 10.128.44.38 (for 
> #4) failed. System.ComponentModel.Win32Exception The client and server 
> cannot communicate, because they do not possess a common algorithm
>
>
> 09:18:08:8209 fiddler.network.https> HTTPS handshake to 10.128.44.38 (for 
> #5) failed. System.ComponentModel.Win32Exception The client and server 
> cannot communicate, because they do not possess a common algorithm
>
>
> 09:21:23:7477 fiddler.network.https> HTTPS handshake to 10.128.44.38 (for 
> #6) failed. System.ComponentModel.Win32Exception The client and server 
> cannot communicate, because they do not possess a common algorithm
>
>
> 14:38:02:7271 fiddler.network.https> HTTPS handshake to 10.128.44.37 (for 
> #2) failed. System.ComponentModel.Win32Exception The client and server 
> cannot communicate, because they do not possess a common algorithm
>
>
> I should probably add that to be FIPS 140-2 compliant the server have the 
> following:
> Protocols: TLS 1.0, TLS 1.1, TLS 1.2
> Ciphers Enabled: Triple DES 168, AES 128/128, AES 256/256
> Hashes Enabled: SHA, SHA 256, SHA 384, SHA 512
> Key Exchanges: PKCS, ECDH
>
> SSL Cipher Suite Order changed:
>
> TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA384_P521,TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA384_P384,TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA384_P256,TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA_P521,TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA_P384,TLS_ECDHE_RSA_WITH_AES_256_CBC_SHA_P256,TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA256_P521,TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA_P521,TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA256_P384,TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA256_P256,TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA_P384,TLS_ECDHE_RSA_WITH_AES_128_CBC_SHA_P256,TLS_ECDHE_ECDSA_WITH_AES_256_GCM_SHA384_P521,TLS_ECDHE_ECDSA_WITH_AES_256_GCM_SHA384_P384,TLS_ECDHE_ECDSA_WITH_AES_128_GCM_SHA256_P521,TLS_ECDHE_ECDSA_WITH_AES_128_GCM_SHA256_P384,TLS_ECDHE_ECDSA_WITH_AES_128_GCM_SHA256_P256,TLS_ECDHE_ECDSA_WITH_AES_256_CBC_SHA384_P521,TLS_ECDHE_ECDSA_WITH_AES_256_CBC_SHA384_P384,TLS_ECDHE_ECDSA_WITH_AES_256_CBC_SHA_P521,TLS_ECDHE_ECDSA_WITH_AES_256_CBC_SHA_P384,TLS_ECDHE_ECDSA_WITH_AES_256_CBC_SHA_P256,TLS_ECDHE_ECDSA_WITH_AES_128_CBC_SHA256_P521,TLS_ECDHE_ECDSA_WITH_AES_128_CBC_SHA256_P384,TLS_ECDHE_ECDSA_WITH_AES_128_CBC_SHA256_P256,TLS_ECDHE_ECDSA_WITH_AES_128_CBC_SHA_P521,TLS_ECDHE_ECDSA_WITH_AES_128_CBC_SHA_P384,TLS_ECDHE_ECDSA_WITH_AES_128_CBC_SHA_P256,TLS_DHE_DSS_WITH_AES_256_CBC_SHA256,TLS_DHE_DSS_WITH_AES_256_CBC_SHA,TLS_DHE_DSS_WITH_AES_128_CBC_SHA256,TLS_DHE_DSS_WITH_AES_128_CBC_SHA,TLS_DHE_DSS_WITH_3DES_EDE_CBC_SHA,TLS_RSA_WITH_AES_256_CBC_SHA256,TLS_RSA_WITH_AES_256_CBC_SHA,TLS_RSA_WITH_AES_128_CBC_SHA256,TLS_RSA_WITH_AES_128_CBC_SHA,TLS_RSA_WITH_3DES_EDE_CBC_SHA
>
>
> On Tuesday, June 7, 2016 at 7:03:03 PM UTC+2, Matt Davis wrote:
>>
>> Seriously- best thing you could do is figure out why Fiddler isn't 
>> working for you and get a trace... Knowing where it's failing in the 
>> process can really narrow some things down.
>>
>> On Tuesday, June 7, 2016 at 9:18:43 AM UTC-7, J Hawkesworth wrote:
>>>
>>> Sorry, I don't have a specific suggestion where to look.  Sometimes I 
>>> toss all the event logs and then poke things rather than filter for a 
>>> specific event category.
>>>
>>> One of my colleagues tells me there's an rc6 for pywinrm 0.2 - might be 
>>> worth trying that if you aren't on it already.
>>>
>>> On Tuesday, June 7, 2016 at 4:32:19 PM UTC+1, Mike Fennemore wrote:
>>>>
>>>> Yes have seen the articles but this was a properly sysprepped template. 
>>>> Have recreated listeners, changed self-signed cert and still seems to 
>>>> yield 
>>>> the same result. 
>>>>
>>>> Jon any particular logs I should focus on? The Windows Remote 
>>>> Management and security logs don't seem to show anything out of the 
>>>> ordinary.
>>>> On 07 Jun 2016 4:04 PM, "Christoph Wegener" <[email protected]> wrote:
>>>>
>>>>> If you are referring to cloning a Windows machine without proper 
>>>>> sysprep usage then that's very well possible. I remember seeing some 
>>>>> WinRM 
>>>>> blogs where people had problems due to duplicate SIDs ... not 100% sure 
>>>>> though.
>>>>>
>>>>> On Monday, June 6, 2016 at 10:20:21 PM UTC+10, 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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>>>>> For more options, visit https://groups.google.com/d/optout.
>>>>>
>>>>

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