Sync problems: Training calendar runs don't show up, workouts don't sync at all

For the past few weeks I've been unable to get my training plan from Garmin Connect to show up correctly on my Forerunner 235. When I navigate on the watch to "Training Calendar", it says to download your training calendar from Garmin Connect. I've tried this a gazillion times. I've wiped the entire watch back to factory settings multiple times, I've canceled and deleted my training plans and restarted with a different plan... without fail, none of the workouts show up in the training calendar on the watch. They are, however, hiding in the workouts section.

I've also discovered that new workouts that I make online with Garmin Connect aren't being synced. I've specifically gone into the app, selected the individual workout, sent it to the device, and Garmin Connect says it worked, the watch shows a transfer successfully finishes... no new workouts.

Anyone else having similar issues? And any idea how to fix it? I'm getting frustrated, the calendar view on the watch is key to keeping me on track.