Mostly posting this in case others are experiencing it as I think I figure out my root cause being the Sectigo/Comodo root certificate that expired on 2020/05/30. More info here: https://nakedsecurity.sophos.com/2020/06/02/the-mystery-of-the-expiring-sectigo-web-certificate/
I have a personal skill that, among other things, allows me to play music that I host on a server. All of my Echos receive the playback error. The Dots and two different types of Shows, all play without error.
I collected a packet trace of the Echo failure and was able to see the Certificate Expired error in the TLS 1.2 handshake (after wasting several days because it failed at the same time I was making code changes, so I assumed it was my work).
My cert is a Comodo cert. It was due to be renewed next month, so I will just do it sooner.