1050 Ride Upload Connect Issue

My Edge 1050 won't upload to Connect unless I close and restart the app.  If the app was already running no syncing will happen.  

This is very annoying and I noticed that my Fenix 6 watch works seamlessly every time making me think it is the 1050.  I tried remove and reconnecting the 1050 to Connect 3x with no effect.

Confused and frustrated.