I encountered the Microsoft Double Hopping issue recently when attempting to automate a Remote Desktop Services deployment.

I first used the basic login mechanism and ran a simple playbook to check the Remote Desktop Service

 - hosts: adserver
   gather_facts: no
     - win_shell: Get-rdserver

The results were weird. It didn't error ou. Just said it could not find the RD Connection Broker. But the broker was the server I was connecting to??

 "stderr": "get-rdserver : The RD Connection Broker server is not available.
 Verify that you can connect to
 the RD Connection Broker server.
 At line:1 char:1

If I run this same command from the Windows Server it works !??

  > get-rdserver
     Server                                             Roles
    ------                                             -----                                          

After some web searching, it became clear the issue was double hopping.

The Ansible Windows Automation documentation says the following about the issue.

Set ansible_winrm_transport to credssp or kerberos (with ansible_winrm_kerberos_delegation=true) to bypass the double hop issue and access network resources

I set the winrm transport protocol to credSSP, after enabling credSSP WinRM support, using the Ansible Winrm configuration script. I'm too lazy to setup kerberos on my Ansible server. Happy to report ... IT WORKED!

Note to self: Always use Kerberos or CredSSP when doing Ansible Automation for Windows!