Unable to Remote PowerShell between 2 Windows 10 Pro workgroup computers

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Between my home systems I've run Enable-PSRemoting without errors and it reports back that everything is ready. I've verified this manually in the firewall, registry and service. Have verified the connection is fine with Test-WSMan successfully. I have created local administrator accounts on the sytems and ensured they can login successfully doing a loopback Enter-PSSessoin. I have added the remote IP to TrustedHosts. I verified both systems networks are Private. DNS is good to go.

I'm using the command Enter-PSSession -ComputerName $a -Credential $a\user and enter the password correctly. No matter what I do I can't get past

Enter-PSSession : Connecting to remote server naz failed with the following error message : The WinRM client cannot process the request. If the authentication scheme is different from Kerberos, or if the client computer is not joined to a domain, then HTTPS transport must be used or the destination machine must be added to the TrustedHosts configuration setting. Use winrm.cmd to configure TrustedHosts. Note that computers in the TrustedHosts list might not be authenticated. You can get more information about that by running the following command: winrm help config. For more information, see the about_Remote_Troubleshooting Help topic.

I can't find any errors in the event log of the remote system. I also verified our time is sync'd. Both systems are running Windows 10 Pro 64bit with latest Windows Updates. Both primary user accounts are tied to Microsoft accounts.

Ideas? (It's easier to fix my wife's stuff via PowerShell than VNC sometimes)

@Michael-Bazdell,

From the error message I'm going to assume an authentication issue. Since your home computer is probably not joined to your domain. You'll probably need to enable WinRM for HTTPS. You can use this link to help: https://support.microsoft.com/en-us/help/2019527/how-to-configure-winrm-for-https

Verify that on the destination machine's TrustedHosts has the connecting machine's IP configured.

Let's see what results from the above...

Could it be that by the looks of it you're initiating a PS-Session to a computer called 'naz' however you've added the IP and not the computer name to the TrustedHosts, for $a set the variable to a string of the IP rather than the hostname e.g. $a = "10.0.0.1"

Okay so I've succeeded in getting it working. I followed Ronnie's link however it assumes you have a CA issuing certificates and WinRM will not function with self-signed certs automatically.

I then found this link http://www.visualstudiogeeks.com/devops/how-to-configure-winrm-for-https-manually which got me 99% of the way there. It misses the part where you need to install the target machine's self-signed certificate into the local machine's Trusted Root Certificate store. Once that was done everything worked.

I've done some testing and have confirmed that between clean installs and non-domain members of

• Windows Server there is no issue in using Kerberos
• Windows 10 to Server there is no issue in using Kerberos
• Server to 10 requires HTTPS
• 10 to 10 requires HTTPS

So it's working now and it's been a real treat to access my lab this way. Thanks for the suggestions!

@Michael-Bazdell,

Way to go!