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I normally export tracks to a GPX file and then manually edit the track name to make sure it's not something weird. The internal track name differs from the filename, ie. in the 5.gpx example, it's...
<name>Beast 600 5</name>
Not sure about RWGPS filenames though. You sure it's not a waypoint or something causing the issue?
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.