Looks like you are trying to connect through a proxy? The winrm connection 
plugin doesn't allow you to explicitly define a proxy in the inventory so 
it would need to be set in the environment variables using the 
http_proxy/http_proxy env vars. You can use the newer psrp connection 
plugin to define a proxy in Ansible like;

[windows]
windows-server

[windows:vars]
ansible_username=username
ansible_pass=pass
ansible_connection=psrp
ansible_psrp_proxy=proxyhost:9480

There are some other variables that you can set like 
'ansible_psrp_cert_validation' but have a look at the docs for more info 
https://docs.ansible.com/ansible/latest/plugins/connection/psrp.html.

Thanks

Jordan

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