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Yes, done that. But it doesn’t seem to go back and retrieve files that haven’t been transferred, so can you manually push rides from Zwift to Strava?
Edit: I’ll do the .fit file thing. The system seems slightly unstable.
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On my phone it takes an age to upload, I think the servers are probably having a nightmare. I push to Strava fine, but if it's not working you could push to Garmin then pull Strava from there (or something similar). If you can get one zwift sync working then Strava/TP/Garmin servers may be more reliable.
Edit: sorry, just reread your post - I don't think you can push old files manually.
Have you disconnected and reconnected them?