I started getting "An error occurred with your upload. Please try again." a couple of days ago while trying to manually import a file. I tried the same ride in gpx format, as well as a previous ride that did work and still got the same result. So, I waited a couple of days and tried again thinking maybe there was something wrong with the website. No luck. Does anyone have a solution to this problem for me? I've tried to navigate the help page for Garmin Connect but still haven't found a way to send a message to support so I thought I would try this. Thank you for any advice/help with this problem.
The issue that you are describing was escalated to the Garmin Connect team and should now be resolved. There is more information and discussion of this issue in this thread: