Spectator messages only arrive at end of workout, or not at all

Since the software update to 5.07, I've been having a lot of trouble receiving spectator messages. I've experienced two types of issues:

  • The message arrives only after the workout has been ended, sometimes an hour after send. The message pops up once you enter the screens to review post-workout stats.
  • When the spectator message is sent, the watch says "Live Track Disconnected," then a minute later "Connected," but the message never arrives.  It seems like maybe there is some error happening on the watch/Garmin handshake that trips the watch into an error state?

In both cases, I had full LTE connectivity in an area with excellent signal.

Any suggestions on how to fix, or how to best escalate?