I thought perhaps one of my scheduled workouts may be corrupt, so tried sending some rather than all ten of my currently-scheduled workouts. Turns out I can send any 9 of my workouts to the calendar, but the timeout error happens whenever I attempt to send 10. I don't believe it's related to storage space on my watch, as the error happens before Garmin Connect even attempts to launch Garmin Express i.e. it fails when attempting to load up my sync-queue (before launching Garmin Express to process said queue).
