WorkSpaces - Unable to connect (This may be caused by current updates)

Hello!

I'm starting to see an issue with a few of my Windows WorkSpaces with the AlwaysOn running mode. I have about 30 workspaces that reboot daily during a maintenance window. A few are not coming back up and show as an unhealthy state. When the user tries to login in the morning, they get the standard 'Unable to connect, please contact IT support' message only now it says, 'This may be caused by current updates.' I can reboot one and after a stressful 10 minutes the user is able to log in again. However, I have another user's workspace I would have to restore and even rebuild to get it back to an available state, until I switched their running mode to AutoStop.

What does this message mean? How can I resolve this without coming into work in the morning having a number of workspaces to reboot?