Why does remote desktop ask the for password again?

I connect to multiple remote desktop virtual machines on a regular basis. The first time it asks me for my username/password, I click the checkbox to remember them, and it never asks me again.

Besides for one machine, I get taken to the Windows login screen and have to reenter the password. This is highly frustrating, especially as the Windows login screen does not allow copy-paste. It’s not part of a domain. Windows 2025.

What I’ve tried:

  • Clearing saved credentials.
  • gpedit.msc: “Always prompt for password upon connection” = Disabled.
  • gpedit.msc: “Turn on Virtualization Based Security” = Disabled.
  • Connecting using Username=Administrator, and also Username=<computername>Administrator.
  • Disable Credential Guard (registry).
  • gpedit.msc: “Require use of specific security layer for remote (RDP) connections” = RDP.
  • gpedit.msc: “Credentials Delegation” = “Allow delegating” (3 similar settings).
  • Create a .rdp file with prompt for credentials:i:0.
  • Cnforce Network Level Authentication and also don’t enforce.

Here’s a screenshot of the login screen that I’d like to avoid:

Windows Login Screen