Issue w/ planned workouts

I usually plan my next workouts 2 weeks in advance (when I receive from my coach). I've been doing this for years without any issue.

So on 16/Jun I've programmed my upcoming workouts and everything looked normal until last weekend when my Saturday workout did not show up. I've manually uploaded it to my watch without any issue but this week's workouts are not showing up and when I check the training calendar on the watch it asks me to connect with Garmin Connect but after re-syncing the watch the issue persists.

Any suggestion?

TIA,