It sounds like a network issue.

Here's a few things you could try:

1/ See Chris Church's suggestion on this thread for a curl command to test 
the communication:

https://groups.google.com/d/msgid/ansible-project/6e7dd49d-d56b-4f2e-8254-9ab0fd2a96f8%40googlegroups.com?utm_medium=email&utm_source=footer

2/ Check you are using the correct port 5986 for https, 5985 for http

3/ Check your machine names are resolvable by your local dns.

4/ Check the windows event log on your managed hosts.  When things are 
working there will be a login event.

5/ run with -vvvvv to see all the communication logging between ansible and 
your managed windows hosts.

3/ Check your machine names are resolvable from your Ansible master.

4/ Check the windows event log on your managed hosts.  When things are 
working, there will be a login event.  If there's no login event its 
probably not finished setting up the communications channel.

5/ run ansible-playbook -vvvvv to see all the communication logging between 
ansible and your managed windows machine.

Hope this helps,

Jon

On Saturday, February 7, 2015 at 6:23:35 PM UTC, Dimitri Yioulos wrote:
>
> All,
>
> After ultimately having set up a test Windows Server 2008 R2 box to work 
> with Ansible (it failed at first, but I thought I had solved the problem at 
> the Ansible control), I've tried to get it working on two other Server 
> boxes.  I set these up via the instructions found at 
> http://docs.ansible.com/intro_windows.html.  However, whereas my test 
> server returns "success" to win_ping, the newly set up boxes return 
> "Servername | FAILED => 500 WinRMTransport. [Errno 104] Connection reset by 
> peer".  I've tried everything I can (e.g. disabled Windows Firewall, added 
> a Windows hotfix, etc.), but nothing is working.  Does anyone have any 
> ideas as to why this isn't working?
>
> Many thanks.
>

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