I’ve tried to push my workout to my garmin 530. The workout is scheduled for today, but on my trainer road calendar it says that the workout is scheduled for Garmin, but it should be pushed to garmin. It’s not showing on my garmin calender. Any pointers?
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Syncing to Garmin is finicky, try using Garmin express or sometimes it just takes turning my Garmin off and on several times and syncing for it to finally work
Also see how many workouts are in your Garmin. My workouts stopped syncing at one point. I had 33 pages of old and duplicate workouts. After deleting a bunch syncing resumed. Not sure if there was some limit I hit.
The issue was not how to sync garmin connect to the garmin headunit, but how to get workouts from trainer road to garmin calendar in the first place. The workouts was not showing up in my garmin connect calendar, and in my trainer road calendar it had the status “scheduled to be pushed to garmin” when it should already have been pushet. Anyway, I reconnected my tr and garmin accounts several times and suddenly it just worked. I dont see the logic, but problem solved for me at least.
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i had this problem about a week ago…
it was an odd solution to solve it - say you have pettit scheduled for tomorrow, you need to go into your calendar, go to workouts, schedule pettit for tomorrow from workouts (so effectively you have it in there twice), change it to outside, and that will push to your garmin calendar.
for some reason training plan outside workouts don’t automatically push to the garmin calendar you have to add it individually from the workout menu.
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Hi, I’m having the same problem. Marking workouts as Outside. Nothing happens. Workout is still in “Scheduled for Garmin”. It has worked fine before but stopped working a week ago.
Tried the proposed solution to add a new workout, no change.
Tried to disconnect and reconnect with Garmin without success.
Any suggestions?
Thanks
Dan
Same issue here, did you find a solution?
Happened to me a couple days ago. A support chat said that Garmin was doing some overhauling that seemed to be causing a problem.
Also offered a workaround. If you’ve already done the TR workout outside before, it is probably still in the Workouts folder on the Garmin device (not Training Calendar). If you select it, the workout will show up on the device just as if TR had sent it to Garmin Connect from the the TR calendar, ready to record and then sync back to TR. Important to know that these items in the Workout folder are the templates for the workouts, not ride files from when you previously did them. So they are indefinitely re-useable, it seems. When you complete the workout outside it gets back to your TR Career page in the normal way.
Helpful to know there’s more than one way to get a fresh copy of a workout template ready to go on your device.
Thanks for your reply, It was an actual problem with the workout having more than 50 steps, which caused the issue. I had to replace it with another similar workout
I’m having this problem. Mansfield -2 shows as scheduled for Garmin but it is not in my Garmin Connect Calendar. Very frustrating
Sorry for the trouble, the Forum isn’t the best place to ‘get to the bottom of’ an issue that may be TR software or Garmin related, as it can be super device/version specific. Support knows best and is the quickest to provide up-to-date info (and in this instance, the action items to help). 
From the ‘Welcome to the TrainerRoad Forum’ Page:
Have a question about the app, your training plan, or device? Reach out to support@trainerroad.com instead of posting here. Our support team has the best visibility and insight into your devices, workouts and adaptations, and will help get you the most efficient and effective answer to your question.
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I think this is the problem! I had a similar experience with Venezuela and changing it to The Needles, which instantly pushed to Garmin Connect.
I little off topic but is it possible to do a pushed outdoor workout in the middle of a ride and have all of it recorded as one ride?
Yes you can start a workout mid ride. Garmin with create a new lap when you start it and then process with the scheduled steps
In case it helps those that search the forum for this problem. Confirmed, a workout with a lot of steps (i.e. pretty much any workout with lots of short bursts) will not sync to Garmin as of 10/2023.
For me it was Pic Lorry (15-15s). As soon as I scheduled a different workout (ANY workout with a smaller number of steps) it immediately synced to Garmin.
Since this is a limitation of the TR–> Garmin sync, perhaps it should be in the instructions for syncing workouts? In reality, a workout like Pic Lorry is probably best done indoors anyway.
-edit: same thing happened today with Sassafras +2. These high rep # high set # over under workouts must just be too big or complex for Garmin connect to handle?
My solution: I substituted Hawk’s Bill (1hr VO2 O/U) which is about half the Sassafras +2 (2hr VO2 O/U) workout and will just do it twice. Close enough.