Yes, I just had a similar problem: a pushed-to-outside workout failed to upload to TR. [It also did not load to Strava.]
If you want to upload the ride manually, then connect bolt to the computer with a usb; use Android File Transfer.app to upload the file from bolt to computer; then use Strava to manually upload the saved file; from there, TR will pull the workout.
It’s a bit of a pain, but it worked for me last night.