Spectator Messaging - not working at all

I originally thought this was only when Power Guide was on but it’s actually always. 

This is not a "solution," but for me I've noticed that after the activity ends, messages will often come all at once the next time I turn on my Edge. Do you see the same behavior?

No, for me messages end in a black hole and never show up.
One more bug which Garmin is probably aware of but will deny it exists ;)

I am having the same thing happen.  Not sure if it’s because the Garmin connects to Wifi after the ride at home or it’s just a matter of the next time I turn it on.

Update - the last few times this has happened I have force quit the Connect app and relaunched it, and then started getting messages.

all right...seems the feature is unreliable. If i can't trust it to work i won't tell anybody to send me such messages. I'll check again in a year or so, maybe it works after a couple of firmware updates.

I received a message from Garmin today that they have released a fix via the Connect app (version 4.68) and that they can’t reproduce the issue anymore. I’m going to give it a shot during my next ride but please do report back if you do!