This problem has been going on for about 2 weeks now. I will modify my training calendar either on Web view or on iOS app view, say, adding a new scheduled workout to today/tomorrow. It does not matter how many times I press sync either on the app or directly on the phone, this new planned activity will NOT show up on my watch until I completely power down and restart my watch. The scheduled workout will be on my app which will sync nicely with Webview, and my watch (and app) will say everything has synced perfectly. Completed workouts, new Spotify songs, etc, all sync nicely. But the updated calendar refuses to update.
This is extremely annoying.
Forerunner 745 (Joining the Beta program - now 12.0 did not make this any better.)