This is a known issue with Chrome and has been going on for a while.
I found this workaround which may help:
I'm still having the issue but I have found a workaround.
1. Type your password anyway even if it doesn't update.
2. Press Alt+Tab multiple times until all the password looks to be in.
It seems like the UI event is not firing when typing. Changing the focus window and coming back updates it. Not an ideal solution, but it goes from taking 1 minute to see your password, to less then 10 seconds.
From here
From here