[coolness]

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

[MereInterest]

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.

[hulitu]

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

[snmx999]

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