Count me with others in here where the skill used to work (though it would very often give me the "server online but I could not connect error) and now just says, “Playing XXXXXX by XXXX on [my server]” and then silence.
When one of my Echo reaches the point of asserting that it is playing but no music is emitted, I power cycle the Echo. Give it a good 30 seconds powered down. After powering it back up, I ask the Echo to ask Plex to change server, then ask Echo to ask Plex to change player, Then I ask Echo to ask Plex play the album Dark Side of the Moon. Nine out of ten times that returns the unit back to a working status. The one out of ten times requires I do all of the aforementioned steps but add/insert delete, and then subsequently re-add, the Plex skill during the powered off state.
I had an issue like this a while back… I would tell Alexa to play a song from my Plex music library, Alexa would say “Now playing {whatever the song was},” but then nothing happened. No music, no error, nothing. The strange part was that a few specific songs did consistently work, but most did not.
I finally figured out that the Amazon Echo device only supported MP3s. All my music was MP3s, but if I looked at Plex’s info window for the songs that worked, there was a “Container: MP3” line that was missing from the info of the songs that didn’t work. So even though it was an MP3, Alexa didn’t realize it because that MP3 flag was missing. I was able to fix it by telling Plex to re-analyze my entire Music library. It took awhile, but when it was done, all my music played correctly when I asked Alexa to play it.
A few more details, and the cause, can be found in my original forum thread about it: Plex Music on Amazon Echo Auto - #7 by dawieg
I don’t know if any of this applies to your issue, but since the symptoms seemed similar, I thought I’d share the knowledge I’d gained.
I have the same issue. I have two 2nd generation Echo’s running as a stereo pair with an Echo Sub. Always worked perfectly to have Alexa play music from PLEX from Windows 10 media server. For a long time now, Alexa recognizes the PC/Server, the song/album/artist titles, library radio, etc., it says it is now playing… then nothing ever happens, just silence. So frustrating. Doesn’t work at all. Used to work so great. Now I have two bookends and zero sound from my PLEX library going through the Echo devices. Talk to Alexa who responds perfectly, then… nothing. What changed? It is a PLEX pass feature now? An API issue? I don’t know where to turn. I’m going through the community threads and it appears I’m not alone. 10.22.2021
No, not a PLEX Pass feature. I have one and have the problem.
I suspect that it’s some sort of network/firewall issue but I gave up trying to fix it on my remote QNAP server and loaded Plex on a local Win 10 device which is working fine (saying which will be the kiss of death, of course)
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I couldn’t be any more local. The Echo’s are left and right of my All-in-one PC/monitor. I have tried turning off the firewall, reinvoking the Alexa skill, reinstalling Plex, etc. Last night tried the reanalyze entire music database suggestion. Still silence. Nothing about this setup, including firewall, is any different than it ever was when it worked flawlessly. Either Windows update or a Plex update or both either working with or against eachother has caused the problem, or something else no longer works the way it did. I just tried having Alexa play music or a movie on FireTV, nothing. The last time she said, “Enjoy watching xxx on Microsoft Edge” when I specified FireTV, but still nothing. Ideas?
I have PMS Version 1.24.4.5081 - up to date as of 10/23/2021 7:44 PM Pacific.
Where do you find a model number for the 2nd generation Echo’s??? I can’t find a model number for the 2nd generation echo’s, certainly not on either device, nor on my original Amazon order, or by Googling anything about it on the Internet, YouTube, here on the PLEX forums, etc. I have seen 1st gen model numbers here, but not 2nd. It’s just the 2nd generation taller echo. Two of them connected as a stereo pair to an echo sub. Works for all streaming services except PLEX. Used to work great. Now silent. Tried everything such as reinstalling PLEX, disabling and reenabling the Alexa skill, etc. Re-analyzing the PLEX music database… Just seems like it’s never going to come back. Day after day, week after week. No luck, and I try daily.
This just started happening to me too. I believe mine is a 1st generation Echo taller device. My other devices work perfectly but this one just stopped working. I tell Alexa to have Plex shuffle a playlist and it replies “Shuffling the playlist XX” but then nothing. Definitely seems like a bug was introduced that is impacting certain Echo devices only.
Tried the solutions above but nothing is working.
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Plex just updated to Version 1.24.5.5173. Still no Alexa/Plex streaming to Amazon 2nd gen Echo’s running as a stereo pair with an Echo Sub. Just silence after Alexa announces what is “now” playing, but isn’t. Just found out it still streams to ONE Echo or Echo Dot (both 2nd gen) just fine, but go back to stereo pair and nothing again. Maddening.
Most likely related: Plex not playing music on first generation Echo devices
Maybe if we can get the info collected for the devs it’ll help resolve it faster, so I’m going to try to link the threads in a collating effort. For those who have this issue and haven’t yet reported your generation echo devices could you please?
@towerpower - The model numbers are on the bottoms of the devices, but they’re REALLY faint and hard to read unless you shine a flashlight on it. For my old eyeballs, I had to shine it at an angle and have someone take a pic and then check the pic to decipher the model. To check the “generation”, all I did was take the model number I finally deciphered and “googled” it. Hope that helps!
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I know I have two 2nd generation Echo’s because it’s right on the order from Amazon. I will try the flashlight thing but I don’t think there’s a model number printed on them. Just checked, still nothing plays on 11.2.2021.
Similar issue here.
About a month or so ago, the Plex skill on Alexa stopped working on our main Amazon Echo. Alexa announces it is playing the requested album, but does not actually play it. It continues to work on our 3rd generation Echo dots elsewhere in the house, but we have noticed that it does not announce the server name (we only have one Plex server, on a WD MyCloud Home) on the main Amazon Echo, where as it does on the Echo dots. The main device is set to the only Plex server we have, and if asked, it confirms it is connected. We can only assume that something has changed that means this skill no longer works on an original Amazon Echo? It’s very frustrating because it was working perfectly up until about 4-6 weeks ago.
Also noticed in the log file - (Capabilities) Platform ‘Alexa’ not matched by plugin platform requirements - which suggests they changed something that has now broken the skill on certain (older) models!!?!
Let’s Encrypt certificate expired 9/30/2021, coinciding with onset of 1st gen Echo and Amazon Tap problem
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So, what can be done? Will anyone do anything to fix this? Whose problem is it? Amazon’s or Plex?
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?
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if this was a certificate issue, this seemed to indicate there would be CERT errors (incomplete TLS handshake) in your logs - SSL Certificate Errors
I don’t have any CERT errors in my logs - post if any of you find CERT errors
perhaps @ChuckPa could weigh in on these Gen 1 echo not playing issues being related to certificate errors
I believe the authentication attempt is taking place and failing in code outside our visibility and control.
When using the Emby skill for Alexa where I must provide the cert, I continue to have no trouble with music on the Echo, so there is no problem inherent to the 1st gen device for that very similar skill. Unlike with Emby, we have no involvement in Plex authentication for the Echo/Alexa player.
The Plex for Tivo skill that failed around the same time had a workaround of telling Plex on the TiVo player not to authenticate my Plex server if it is on the same local network. But there are no settings like that available to us for Alexa devices.
Without being able to look at the Plex code that is invoked by Alexa on 1st gen devices (and I assume that code is in the cloud), that’s about all I can say. But the timing and the nature of the problem is coincidental with the expired Let’s Encrypt cert that has been the root cause of so many other problems.
There are no numbers on the taller 2nd Gen Echo’s flashlight or magnifying glass or any other way. There are faint model numbers and other text on the bottom of the Echo Dots 2nd gen. I have a case on mine, and when you remove the case, that’s where you find the numbers on the bottom of the actual Echo Dot. The ‘case’ is built into the taller Echo’s, it’s rubber on the bottom, no numbers. In messing with that, I thought, try the 2nd gen Echo Dot with your PLEX music. It works. So now I’m trying re-doing my 2 Echo’s and Echo subs from scratch and see what happens. Not just the re-upping the Alexa skill, but telling Alexa to forget the devices and I will get them back online once they are a stereo pair with the echo sub again and fingers crossed it might get the music streaming again. Will report back.
No luck. Well, some. Alexa will play PLEX music through ONE 2nd generation echo (or one Echo Dot), but not through two as a stereo pair w/an Echo Sub. Just silence. Still where I started. Ask Alexa to play through the stereo pair of Echo’s with a stereo sub, she knows the system, says it’s playing, but nothing is. With one Echo or Echo Dot (2nd gen) Alexa can get Plex music to fire right up. I did everything you can do as far as having all the devices unauthorized and reauthorized from scratch, created the pair, added the sub, redid the Alexa skill, etc., etc., nothing makes any difference or helps. What I didn’t know is that it would have still worked with one Echo or Echo Dot, but not the stereo pair any longer. All other services Spotify, Prime, Pandora work fine with the stereo pair and sub. Left a complaint update with the Alexa skill in the app as well. Very frustrated.
I find exactly the same thing happening, if i have a stereo pair of echo dots it will only play music files encoded as MP3 if the files are encoded as FLAC it will play one track then stop.
my echo dots are 3rd generation
If i break the stereo pair and only play in mono using either of the echo dots then the files play perfectly.
I have tried creating an alexa profile which transcodes everything to mp3 but it didnt make any difference, it did not appear to do any transcoding and presumably it queries the playback device to discover its capabilities and uses that in preference to the profile.
