After further review it looks like starship is creating a pvxwin32.exe session when it is attempting to go back into MAS after processing the package in Starship. It seem to have to do with the writing on the tracking numbers into MAS and popping the tracking screen. I looks like some handle is being lost. Luckily it is not happening every time. At this point the only solution it to kill the pvxwin session and restart both MAS90 and Starship.