I had to reauthorize my bolt/wahoo app to strava earlier this year. The headunit has always uploaded by wifi when I got home. It was working in feb, and all of a sudden in march or april I noticed a ride didn’t sync. It was uploading to dropbox just fine, but the strava link stopped working (but didn’t show an error either). First time I’ve had to fiddle with it in 2 years I think – maybe exactly 2 years now that I think about it more (xmas gift; first ride in feb or march, weather-dependent).
As for TR sync’ing from strava, seemed a bit slow this month pulling in outdoor rides from strava. I could sit down at my computer and see them on intervals.icu, but waited an hour or more for it show up in TR. Not sure if it’s a pattern or fluke yet, but I’m assuming fluke.