I have noticed this behavior since the earliest days of Win10 beta, I think even back in the days of Win8. I beta test Windows so I dual-boot a lot. The problem here lies in the fact that the iReboot Service does not Start, even though it is set to Automatic. What happens is the program loads the tray icon when Win10 boots up, but the corresponding service does not start, that's why you will not get any right-click menu. The work-around for this is to open Services, find iReboot, then Start it. I hope the developers can find a way to fix this. It's very annoying. Once the service is started, you have right-menu functionality and use the program as intended. I know this thread is a month old, I was hoping by this time a newer version would have been released and have fixed this by now. Hoping somebody finds this post useful.