Hi Greg Hawthorne,
It almost always happens because Windows temporarily drops the Wi-Fi connection on the lock/login screen, meaning it literally cannot reach Microsoft's servers to verify your password hash for the first time. Here is how to get past it:
1. The Quick Fix (Force the network): While you are on the lock screen, look at the bottom right corner. Click the Network icon and manually force it to connect to your Wi-Fi (or temporarily plug in an Ethernet cable). Once you visually confirm it has an active internet connection on that specific screen, try entering the password again.
2. The IT Pro Alternative (Bulletproof RDP): Honestly, using a Microsoft Account for RDP is notoriously fragile precisely because of NLA and Hello conflicts. The most stable, headache-free way to handle this is to create a dedicated Local Admin account just for remote access.
Open Command Prompt as Admin and run: net user LocalRDP YourSecurePassword! /add net localgroup Administrators LocalRDP /add
Now, just RDP into the machine using .\LocalRDP as the username. It completely bypasses all Microsoft Account sync issues.
Try forcing the network on the lock screen first, but keep the Local Admin route in your back pocket.