My account works fine, but my son’s does not. The workout will post but no image. We have un-linked and re-linked multiple times. Unless I’m missing something, his settings are exactly the same as mine, for both our TR and Strava accounts. Thx!
I suggest that you contact firstname.lastname@example.org so they can get a full look at the issue.
Just a note, if the rides are set to be viewed by “only you” on Strava the image does not show up. I guess that’s because it’s an advertisement, and no sense advertising to you, you’re already customer.
I second the “contact support” solution. I’ve contacted support once or twice about ride images that didn’t sync over and they were able to fix it.
My account did the same a while back.
TR support advised me to unlink my Strava account from TR and then relink again.
Every workout has had the image since.
Hope it’s also a quick fix for you.