I have observed over the last month or so of manually uploading workouts that if i have more than 2 .fit files of workouts, they fail.
An interesting observation is that it won't fail if the start points are considerably far off(500m+).
There could be a flag check for start point of the workout that is returning an already uploaded response, but this check should also include the timestamp.
My use case is I start my wame up from point A and do a mile loop. Then after a good 30mins or drills etc which are not tracked, I begin my run from within the same vicinity.
While the use case seems pretty common, I'm curious if there's something wrong with what I'm doing.