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Can't send workouts to devices; never gets past "Preparing Workout"

I have both a 310xt and an Edge 810. I can't send workouts to either device from Garmin Connect. I select the workout, click Send to Device, select the device, click OK, and GC says "Preparing Workout" and just sits there forever.

I care more about the Edge 810 at this point. It's connected and Express sees it just fine. Anyone know how to troubleshoot this?

Jason