It’s not impossible. You can still get what you want right now, it just will take a few more steps.
I have the same issue. Using a macbook pro. Unable to sync my ride from Zwift with TR. Have tried editing the title in Strava, manually importing the gpx file from Strava, manually importing the fit file from Zwift, all without success.
For me, this is a “it just has to work” feature with regards to syncing rides from various sources if I intend to use TR as my single source of training analysis. Any help is appreciated, cheers.
I have been in communication with support about this, it seems if you use TR then Zwift afterwards it might not upload because the time stamp is too close together. All my other Zwift rides have uploaded, but these a done on different days to TR. I hope TR manage to do a patch for this in the future.
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That seems to be the case here. Rode on Zwift today, ride synced without issue. The previous ride was immediately after a TR ride.
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This bug still has not been fixed. It isn’t Zwift-specific; any ride from Strava after a ramp test will not sync correctly. Any attempt to upload the ride manually leads to an error message that it is a duplicate. This means the ride has synched but it does not show up in the calendar or as a past ride. Surely the fix is not so hard that this bug is still present two years on? I do not want to have to contact support every time I do a ramp test and then ride after in order to get the ride to show.
Hey! We have this fixed in the beta version of the new TrainerRoad app if you want to become a beta tester and not wait until RN goes to production!
I don’t think the problem has anything to do with the mobile application. This is an issue with syncing - the mobile app is not involved.
The fix will be released when both mobile and desktop apps are updated soon, but getting on the Beta version will just give you access to that fix sooner! Otherwise, you should feel free to sit tight for the update on all platforms shortly. 
This sync issues occurs with the website, so I fail to see how getting the Beta version of the mobile or desktop apps will fix it.
Sorry for the confusion, happy to expand upon that!
So we have duplicate logic within TrainerRoad to filter duplicate rides from syncing into TR (e.g. if you record your ride on your Garmin/Wahoo at the same time as your TrainerRoad ride, you have Ride Sync set up between TR and Garmin, we’ll block the Garmin/Wahoo ride).
How the duplicate logic works is we take the start time and duration of ride A and block any ride that starts within that window. Because the Ramp Test’s start time is showing up as when the cool down begins, there’s an extra 15-20 minutes of time after the Ramp Test where we’ll block rides.
This ‘duplicate language’ bug has since been fixed on desktop versions, and has now been fixed on iOS Beta, although we see you use an Android device for Ramp Tests and workouts. We can get still around it if you hit up support and send us the file for the ride that was blocked, and we know this is arduous to have to do all the time, but we will have Android beta ready soon that prevents you from having to do this!
The bug you describe sounds like it would be very easy to fix. Why has it taken two years (longer for Android)?
Sorry for the delay, definitely wish this stuff was quicker and less complex to work out than it is! We’ve implemented numerous features and fixes since the last mobile app that were higher priority, but we’re glad that the mobile updates are almost ready!
I have been looking in the forum and this was the best thread for Zwift/TR issues.
Yesterday I completed a TR session (Churup - oh man!!) then, after I picked myself off the floor, switched over to Z for an aerobic spin. I had closed TR and reconnected devices to Z.
The Z session has not uploaded to TR calendar to be included in weekly TSS. I have downloaded Z .fit and .gpx files to import into TR but TR states the file is a ‘Duplicate Workout’. Any ideas?