I am seeing this issue with Macs running Sonoma and Connect 2.27.0. I am not sure if Connect is actually causing this but it is currently my prime suspect.
What is happening is this. The Mac boots up, asks for a PW to decrypt the drive and then opens to the Finder no problem. I can also log in using the Local Login option. If I then log out, it brings up Connect and I can log back in no problem.
But (you knew this was coming) if I lock the screen or put the machine to sleep from the Finder, when it wakes up and asks for a password, it will not accept whatever I enter. It acts like I'm entering the wrong password and I can't get past this and must reboot the machine to get back in.
Anyone else seeing this? I have't seen it on any of my machines before Sonoma.