I have hit a lot of s2012R2 machines today using ansible 2.0.0.2 and 
2.0.2.0 so I don't think it is something inherent in ansible.

Connection timed out implies it isn't able to connect to winrm on the 
machine. 

I suggest you try the pywinrm examples directly 

https://github.com/diyan/pywinrm#run-process-with-low-level-api-with-domain-user-disabling-https-cert-validation

Also I'd go looking for firewall changes to make sure the winrm port is 
still open.

Hope this helps,

Jon

On Monday, May 23, 2016 at 5:17:51 PM UTC+1, Dimitri Yioulos wrote:
>
> Hello, all.
>
> Until today, I'd hadn't used our recently updated Ansible (19.4. --> 
> 2.0.2) against our few Windows Server 2012R2 servers but, when I did, I had 
> failures, even when running the simplest modules (e.g. win_ping).  Here's 
> what I get:
>
> Loaded callback minimal of type stdout, v2.0
> <veeambackup11> ESTABLISH WINRM CONNECTION FOR USER: winuser on PORT 5986 
> TO veeambackup11
> veeambackup11 | FAILED! => {
>     "failed": true, 
>     "msg": "ssl: 500 WinRMTransport. [Errno 110] Connection timed out"
> }
>
> I see the "Connection timed out" message, but am puzzled as to why I'm 
> getting it with Ansible version 2.0.2 (the Ansible upgrade is the only 
> thing that's changed in the environment).  Everything worked on both Win2K8 
> and  Win2k12 boxes in version 1.9.4.  In version 2.0.2, everything works on 
> the Win2k8 boxes but, as I said, not on Win2k12.  Has anyone experienced, 
> and solved, this problem, or can otherwise shed some light?
>
> Many thanks.
>

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