I am having the same problem with my Edge 520. I can’t transfer my calendar from either The app or web based Garmin Connect. Workouts are all transferred however. I have removed the app, factory reset…
May be a free storage device issue. I've deleted from my fenix some apps and a training plan that I haven't started yet but it was programed in my Connect calendar. Now I only have my current training plan and it synchronized successfully with my fenix by computer USB connection.
I am having the same problem with my Edge 520. I can’t transfer my calendar from either The app or web based Garmin Connect. Workouts are all transferred however. I have removed the app, factory reset my device, unlinked the phone and started from scratch with no result.
Thank you TrippyZ! I have a Forerunner 220 and my training regimen was not syncing to my watch. I followed TrippyZ's advice by adding a random workout to one of the days in the calendar and then resynced. It worked!