I played 3 courses in August and I am unable to get them to upload to Garmin Connect. I played 5 courses prior and they uploaded with no problem. I contacted Garmin Customer Support in August and their idea was that I keep trying. I've tried once per month when I charge my watch, and they still will not upload. I can browse to the scorecard folder on the watch and see the XML files for all 8 scorecards, so the data still exists on the watch. I've even tried small edits to the XML file (changing the minute in the timestamp for when the round was started) in order to make the scorecard seem "updated" to the Sync and that has no effect on getting these scores uploaded.
Does anyone have any ideas on what I can try next?