I've had similar issues before:
1. Has the Windows box had configureforansibleremoting.ps1 run on it?

2. Is DNS resolvable for the server?

3. Have you tried running configureforansibleremoting.ps1 with the extra 
arguments to recreate the winrm certificate? 

4. Is the Windows server a VM cloned from a template? 

5. What pywinrm version? 

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