Hi, I'm running Eddie on Windows 8.1 and are experiencing the same. Since this only seems to happen in Windows, I think the root of the problem has to do with the way Windows are using hibernation as default when shutting down, which isn't the case when restarting. It was also a problem in the previous version of Eddie, so after a Windows shutdown the "Start with Windows" hasn't been working during the latest two versions of Eddie (if not manually killing OpenVPN or restarting as mentioned a