Cannot set it to All monitors on macOS High Sierra

One of my users is having an odd issue when using log me in on a mac. This issue just started this week.

They can get a single monitor to work but the moment they switch it to "Multi Monitor" all windows go away and there is no way to bring them to the front. If you force quit log me in it goes back to the single monitor and you can use it again. Tried it both through the web and using the log me in app with the same results.

macOS High Seirra 10.13.6

Macbook Air with Dual monitor setup, don't know if this matters but I'm using two different HDMI adapters. As J5 USB to HDMI and a MiniDisplay port to HDMI adapter.