Because of the fact that an unrelated audio skill, WJST Jet Set Radio, developed the same problem (1st gen Alexas only) at the same time (9/30), it could seem like it might be on Amazon’s side.
But the widespread Let’s Encrypt SSL certificate expiration problem on 9/30 mentioned above also affected our Plex for TiVo app, which definitely won’t be updated (it has a workaround by telling TiVo’s Plex app not to insist on a secure connection).
That suggests that Plex might have the Alexa ball in their court.
I chatted with the WJST guy, and he pays a 3rd party UK outfit to put up his skill, so he is unaware of any SSL details. I haven’t found the same problem with any of the major audio skills I use (Pandora, Tunein, iHeart, Somafm).
We haven’t heard from Amazon on this, so we don’t know why the problem occurs only with the 1st gen Echo and the Amazon Tap (a 1st gen and discontinued device).
My best guess is that the code in the version of Plex used on 1st gen has reference to the bad cert. I know that Plex behavior on those two devices was a little different than on my newer Echo Dots, so they might well use different Plex code.
(Previously on PlexDash, if you were playing an album, then told a 1st gen Alexa to stop, the currently playing song did not immediately disappear from the dashboard as it did and does with 2nd and 3rd gen Dots.)
My workaround with the portable and rechargable Tap is to Bluetooth WJST sound to it from a Raspberry Pi (the Tap is basically a Bluetooth speaker with most but not all Alexa capabilities). I can get along without Plex on 1st gen since I have Emby as well. The Emby skill requires you to get your own SSL certificate for your server, which is a huge pain in the ass to set up, but really pays off now.
But I would much prefer to have the Amazon devices work the way they should.
