No matter what I do I keep getting the same issue. When trying to connect from my management server to the headless HOST I get the following.

This is the Host Machine.

This is the management machine which is a VM.

I keep going around in circles from everything I have googled. I did enable a virtual nic card which knocked me out and then i could not connect anymore. I was able to remove the vitual interface which caused the box to go back to the physical NIC. I reestablished connectivity to the box and can RDP into it. I can ping each box from one to the other. This tells me I am back on the network and everything is talking except I keep getting the WinRM cannot complete the operation. I am fully prepared to take the lumps due if it is something simple like "have you rebooted". (I have) I have really tried to get this one figured out but lack of experience is eating my lunch. Any pointers would greatly be appreciated.
Manager pinging host:

Host pinging Manager:

Apologies if this format is bad. Pointers on that would be good too. Thank you.