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Does anyone else have trouble with Apple Watch/health app automatically uploading bike rides to Strava? I record my workouts in the fitness app on my watch, which saves workouts to the Activity/Fitness app. This should sync between Strava and Health. The apps are enabled to talk to each other and automatic uploads are enabled as well. All other workouts (ie walk, run) import automatically no problem. With bike rides (“outdoor cycle”), I have to manually hit the import the ride. Pretty annoying!

To troubleshoot, I have disconnected the Strava app from Health/Fitness, deleted the app and redownloaded to my phone and watch. Same thing happens though. Any other activity automatically imports to Strava just fine. But with Bike rides, I have to manually go into Strava on my phone and hit "import". Could this be a bug?

I was about to post this same problem and found your question. I have been having this same issue for a long time on Strava and Apple Watch. This is a problem with all workouts (cycling and running). Sometimes it does automatically upload to Strava (<%5) but more often it does not. I think it really boils down to if Strava is actually running on iPhone whenever you stop the workout on your watch. If Strava is in background and not running, it does not know it needs to upload a file.

Alternative, if you use Strava on watch to record, this does work 90% of the time but sometimes Strava on watch has an issue to upload from watch and you have to manually force it.

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