This has been happening for quite a few months. I create a Run workout on my iPhone or my Mac using the Connect app. I then hit send to device (either on the phone or on my Mac when it's connected with he USB chord). It will say that the workout was send and sometimes the watch will say that the update is received (though not always), but then when I go to look at my list of workouts the new one isn't there. The watch is talking to my phone because I get alerts from other apps on my watch and also when I finish activities they appear on the Connect app on my phone. I've tried deleting some of the workouts on my watch to see if it was a matter of not enough storage for the new workouts to fit but that didn't help. Turning the watch off and on again also didn't seem to help. I'm very hesitant to do something like clear out all of the workouts that are on the watch already because with new workouts not making it to my watch I can sometimes dig up old ones that are similar to what I'm supposed to do. The watch and the phone do seem to be talking to each other so I don't understand why new workouts don't show up.