So basically whenever I restart my OS, "Keep the taskbar on top of other windows" gets reset - why? I have to right click my taskbar everytime, then re-check this box. This didn't used to happen til I updated to 5.0.9344 Thanks!
Need to shut down Windows first From Parallels: Windows is also an Operating System like Mac so whenever you want to close Parallels Desktop you have to shut down Windows first. When Windows shuts down normally it saves all the settings. To shut down Windows click on Start Menu > Turn off Computer/Shut down. So the next time when you restart Windows it will show the same settings. Or it has to recover and reset the settings.
The point of the post wasn't to explain how to shut down Windows. The point is that a loss of settings after shut down of the Virtual Machine most times is due to not shutting down Windows before shutting down the Virtual Machine or quitting Parallels.