Yeah, even with this fixed it's going to be annoying because it first restarts, so you have to stay at the PC to select windows in grub

Full-disk encryption, as useful as it is, also makes this a royal pain. Updates can't be performed unattended, because each restart done during the updates requires providing the password before continuing.

Why don't you let Windows manage the password for you ? It will be safely stored in the Cloud. /s

You can set grub to select the lastly selected menu entry.

I honestly thought the same and kind of just gave up the idea of hitting that at night and being done.

Figured having 4 OS installations was already fairly niche that it was largely a self imposed issue. Looking forward to confirming that this fixes the issue in my use case.