TR has synced the images of workout profiles perfectly to Strava… until today. I have ensured I have the latest versions of both apps. Does anyone know how to fix this?
Hey! If your workouts themselves are still syncing but just not the images, I wonder if there was a privacy setting within Strava that may have changed? I would get in touch with the TrainerRoad support team, they can help you look closely at both of your accounts and see if all the settings are dialed, or if it just requires a re-sync.
Did you get a fix for this. I too have the same issue and did the re-authorization ‘fixes’ recommended by the TR support, but no success
Re-authorisation worked for me, fortunately. It has happened once since, but then the next day worked fine (without me doing anything).
The settings are explained in this blog post → https://support.trainerroad.com/hc/en-us/articles/204620814-Strava
In my case, all it took was to go to Strava Settings → Partner Integrations, set it to “Enabled” and immediately my workouts displayed images! It was super satisfying. 
Sorry for awakening an old thread. 
I’m just a TR noob sorting through all of the things.
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Just a note on this from personal experience.
I have found that sometimes, Strava can have some syncing delays.
This means that randomly, a TR ride will sync but the accompanying black and blue workout profile screen shot doesn’t sync across with it.
This has led me to follow all the usual ‘checks’ for privacy permissions etc only to discover it was all as it should be (and has been for ages).
Then all by itself a few hours (or even the next day in one case) later the image synced across.
To this end, may be worthwhile just waiting a wee while to see if it sorta itself out for you.
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Looks like this has started happening again in the past couple of days. Anyone else?