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Sync Error 910XT and Garmin Express

Garmin Express isn't uploading any data to Garmin Connect for me. I think the problem stems from a long run... When I view history for the run on my watch no lap history shows. To troubleshoot, I removed and re-added my 910xt from Garmin Express. When the watch tried to re-send all activities, the process hung. The status of each activity says "Waiting to upload" except for the run in question which says "Error".

Any advice?

Thanks