Docker – Windows Server 2019 Core install fonts

This link will be helpful in resolving Enter-PSSession (http://jeffgraves.me/2013/10/14/powershell-remoting/) WinRM denies.

For our specific case we did the following:

On the Local machine winrm quickconfig (although this was already configured)

winrm s winrm/config/client '@{TrustedHosts="myservername.domain"}'

On the Remote machine

enable-psremoting -force

Set-PSSessionConfiguration -ShowSecurityDescriptorUI -Name Microsoft.PowerShell -Force

https://stackoverflow.com/questions/16062033/cannot-create-remote-powershell-session-after-enable-psremoting

In fact Windows 2019 is very buggy now. I would suggest avoiding it for now and wait for the new stable release.

According to the Microsoft Evaluation Center:

"We have temporarily removed all media for Windows Server 2019 and Windows Server, version 1809. We have also paused the rollout of the latest feature update to Windows 10 inclusive of versions 1809, as we are investigating isolated reports of users missing some files after updating. If you have already downloaded media, please don’t install it and wait until more information is available to proceed. We apologize for any inconvenience this may have caused. We will provide an update when refreshed media is available. For reference, we also have a support article with additional information."

However, you can try a possible workaround - install Windows 2019 in BIOS (Legacy) mode instead of UEFI and then Hyper-V should not cause the boot loop.