Guessing here, since this is not something I've tried

This poster seemed to get the same error as you:  In his case there was a 
proxy involved.  Would there be a proxy in your scenario too?  I think 
there are winrm proxy settings now although this isn't something I've tried.

http://search-devops.com/m/PLILD1J1SKcY32cn&subj=+ansible+project+Ansible+connect+to+Windows+instance+through+proxy

HTH

Jon
On Thursday, 31 March 2016 07:18:56 UTC+1, David O'Brien wrote:
>
> Hi guys,
>
> I'm spinning up EC2 instances on AWS and I'm getting the following error:
>
> TASK [setup] 
> *******************************************************************
> <10.178.73.194> ESTABLISH WINRM CONNECTION FOR USER: Administrator on PORT 
> 5986 TO 10.178.73.194
> fatal: [ip-10-178-73-194.ap-southeast-2.compute.internal]: FAILED! => 
> {"failed": true, "msg": "ssl: 500 WinRMTransport. Tunnel connection failed: 
> 403 Forbidden"}
>
>
> I can telnet just fine to that machine on 5986 and using the same 
> credentials, logged on to Windows I can setup a New-PSSession without 
> issues.
>
> $options = New-PSSessionOption -SkipCACheck -SkipCNCheck -
> SkipRevocationCheck
> New-PSSession -ComputerName "10.178.73.194" -UseSSL -Credential $cred -
> SessionOption $options
>
>
>  Id Name            ComputerName    State         ConfigurationName     
> Availability
>  -- ----            ------------    -----         -----------------     
> ------------
>   4 Session4        10.178.73.194   Opened        Microsoft.PowerShell   
>   Available
>
> Anybody an idea what's happening?
>
> Cheers!
>

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