The only time I've ever seen that behavior is on the first request to a 
brand-new Windows AWS instance. For some reason, the shell creation can 
take up to 30s, much longer than our default operation timeout of ~5s.

You can try increasing the operation and read timeouts by adjusting the 
ansible_winrm_operation_timeout_sec and ansible_winrm_read_timeout_sec 
inventory vars (the read timeout must be > than operation timeout). They're 
set to relatively low values to minimize the "dead host" detection 
interval, and this doesn't typically cause problems in normal operation.

-Matt

On Friday, March 17, 2017 at 3:17:19 AM UTC-7, Michele Viviani wrote:
>
> Hi,
> I do have some problems using Ansible with Windows.
> For many of my servers it works, but for some I'm receiving 
> "HTTPConnectionPool(host='10.10.193.180', port=5985): Read timed out" even 
> if the WinRM configuration is correct. (it's the same as several others)
> More over, if I run a Enter-PSSession myhost.domain.com from another 
> Windows server, it works and after that command also ansible win_ping is 
> responding.
>
> Below my test case
> *************
> [[email protected] ~]# ansible windows -m win_ping
> 10.10.193.180 | UNREACHABLE! => {
>     "changed": false,
>     "msg": "ntlm: HTTPConnectionPool(host='10.229.193.180', port=5985): 
> Read timed out. (read timeout=30)",
>     "unreachable": true
> }
> *************
> Executing successfully  Enter-PSSession myhost.domain.com from a Windows 
> server
> *************
> [[email protected] ~]# ansible windows -m win_ping
> 10.10.193.180 | SUCCESS => {
>     "changed": false,
>     "ping": "pong"
> }
> *************
> here my settings
>
> [[email protected] ~]# ansible --version
> ansible 2.2.1.0
>   config file = /etc/ansible/ansible.cfg
>   configured module search path = Default w/o overrides
> [[email protected] ~]# python -V
> Python 2.7.5
> [[email protected] ~]#
>
> Any ideas/help?
>
> Thanks a lot!!
> Mike
>

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