Thanks @tulsatv, I lost track of that issue in the fray. How would we test the cert expiration theory? Is it as easy as “Disable” encryption in the plex server temporarily for testing? Then if Gen 1 devices work then we know it’s cert related? It’d be really helpful for the devs to weigh in here… Bueller? Bueller?? 
By the way, spoiler alert, disabling encryption on the server under Network settings did NOT fix this issue on Gen 1 devices for me, same API interactions as I outlined here: Plex not playing music on first generation Echo devices - #5 by larryg99.
Here’s some more info that I collected on the subject:
Neato plex status page that I wasn’t personally aware of: https://status.plex.tv/
https://www.echotalk.org/index.php?topic=6043.0
https://blog.dnsimple.com/2021/09/letsencrypt-intermediate-expiration/
This does seem awfully coincidental with the Gen 1 Alexa devices - but how do we prove it?
