Sounds like the USB headset is not connecting correctly and when it does (unless rebooted) there is a corruption between the headset and Windows.
Try this and see if it helps. With the headset connected: go to the Device Manager, RIGHT click on the entry for the headset to highlight it and then Left click "Uninstall" (do not check the box to uninstall drivers
). Then disconnect the headset and restart the PC. After Windows starts, connect the headset and Windows should detect new hardware and reinstall it. This fixes a lot of flakey problems and may take care of your problem.