>From the error message it looks like there is a network proxy being used.
If possible I would try and set things up to not use a proxy to start with 
so you can rule out whether the proxy itself is breaking the communication.
You might wish to try the psrp connection plugin as that has options to 
avoid proxy.
https://docs.ansible.com/ansible/latest/plugins/connection/psrp.html

A couple of useful pages if you need to get into debugging winrm connection
https://www.hurryupandwait.io/blog/understanding-and-troubleshooting-winrm-connection-and-authentication-a-thrill-seekers-guide-to-adventure
https://www.bloggingforlogging.com/2018/10/14/windows-host-through-ssh-bastion-on-ansible/
Also the trouble shooting guide here is helpful too:
https://docs.ansible.com/ansible/latest/user_guide/windows_setup.html#common-winrm-issues

Hope this helps,

Jon

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