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I can imagine anything odd causing Garmin dramas.
These were simple track names though, ie. the one it missed was "5.gpx".
Beast from the East - I remember it the most - it was a 9-part 600k as it was also the first ride I'd taken the shitty 810 on for a backup device. Previously I'd probably just uploaded a single file or not noticed it hadn't copied.
I use ride with GPS and if you have ever had or currently have a 'special' character in the ride title then it won't upload. Been caught out a couple of times without realising.