bumping for @vanstinator . Any updates regarding this or the Google Home Casting incompatibility in the other topic? Thanks.
P.S Discourse is a great addition to the forums and vanilla was garbage. Don’t listen to the haters.
Your Echo device isn’t sending any events back to Alexa Voice Service due to some sort of networking oddity. Due to this our telemetry can’t detect that your connection is bad and try something else. We’re currently developing an updated version of the Plex Alexa skill that will be more intelligent about ordering connections to try to help resolve this issue. I do not have a timeline to share on when this may launch. When it does lets regroup and see if it helps your specific case.
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same to me 
I’m just joining the choir to say that playing music on my Echo Dot doesn’t work.
“Alexa, tell Plex to play music” then she says “OK, playing library radio” but no music plays.
“Alex, tell Plex to play music on my Samsung TV” - that works.
Annoying though because I have decent speakers plugged into the Echo Dot and I don’t want to listen to music through my TV.
And it’s extremely annoying to receive spam emails from the Plex News team like I did today, when it doesn’t bloody work (and hasn’t never bloody worked, despite waiting for it to start working all year) for me and a lot of other people.
Get your music in Plex and enjoy a hands-free music experience with Alexa. Listen to your entire collection, play your own radio stations, and do it without lifting a finger. Whether you want to play a legendary album or a mix from an artist you just love, Plex makes it easy. And, with Amazon Music Storage shutting down in the near future, Plex is the easiest way to have access to your whole library of tunes.
I don’t have an exotic network setup, just a Win 10 Plex media server. Remote access works.
Matt
This has also never worked for me. Typical setup. Didn’t work today - I had mostly given on up this working.
Today, I tried something based on some other posts in other threads. My ISP is comcast, and they are a big IPv6 supporter - so I enabled IPv6 on my computer and clicked the “enable IPv6” in Plex. I restarted Plex, and bingo now it works.
Presumably, the Echo Dot is connecting over IPv6 (which is a public address) to Plex, rather than using the NAT IPv4 address.
Of course, for better or worse, now my computer is essentially public on the internet over IPv6 - you lose some of the security of the NAT framework.
I have 2 Echo Dots on my network and on the one that I used and tested with when setting up my Plex on my Synology NAS (DS216Play) all seem be working fantastic. This one is called “Upstairs”. But on the second one, called “Downstairs” (smart names ;-)) I can ask ALexa to play and more but no sound is sent to this second Echo Dot. It is playing on the Upstairs Echo with my new request but I want it to play on Downstairs. Doesnt work 
We just pushed a fairly major release that contains many under-the-hood changes to improve the robustness of the playback engine. Plex for Alexa
This won’t address specific network issues but it will dramatically improve the playback experience for those who were having sporadic success already. We’ll be shipping more enhancements in the coming weeks and months to further improve the experience.
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I’ve had the problem of Alexa only playing one song then stopping since I got an echo (which I only got due to the Plex integration)
Arrived home today and asked Alexa to play some music through Plex like I usually do, and the music started as usual. But then it played another song, and another!
Assuming this is what fixed it, Thank You! 
Glad to hear!
Need to apply the fix to the Fire TV Cube as well.
Alexa skill updates apply globally to the device install-base. When was the last time you tried to play music? I can check our cloud logs to see what might be going on with your user.
@JoePhelps our skill hasn’t seen your account since August 24. Please try using it again and let me know how it goes.
I tried it this morning after reading the update announcement.
Can you DM me the plex username attached to the skill? I searched on your forum user. Maybe you used a different account?
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To all who have been experiencing dead-air after requesting playback: We’ve shipped a big under-the-hood release today that overhauls how we manage and deal with playback failures and connection types. If you haven’t been around for some months due to issues I’d encourage you to try again and report back.
When I tell Alexa on the Fire TV Cube to tell Plex to play some music, it seems to work ok – it plays more than one song. When I use the Plex app on the Cube to play an album or playlist, it’ll only play one song and stop. (It actually tries to keep playing the song after the end of the song has been reached.) See the thread I referenced above.
Oh you mean the Plex app itself. Sorry I thought we were discussing the skill. Can you please create a new thread with the proper tags? I’m not able to help with FireTV issues and this thread is dedicated to Alexa playback bug reports. I can ping the team if you create a new thread.
@vanstinator I am happy to say that this is now working correctly on my Echo Dot. A huge thank you to the team and yourself. Hopefully Google Home will come next <3
Hey all, I posted this yesterday as a new thread, didn’t see this ongoing discussion:
Server Version#: 1.13.7.5369
Player Version#: latest on amazon
I’ve been using the Alexa skill for a while now to stream music to my 2 echo dots and echo-speaker device (it was also working with the Alexa app on my phone). Suddenly, last week it just stopped. When I do my usual “ask Plex to play music”, it responds as usual (“Enjoy”) but nothing plays. When I check the Activity section of the server, there’s nothing playing. It’s as if it accepts the command in the Alexa skill but doesn’t pass it to the Plex server. (The skill does everything else, i.e. read off new releases, will find the latest release by whatever artist, just not actually play anything)
I installed another Plex server on another Windows machine with the same result. I manually changed the server with the Alexa skill to a friends remote server, and it appears to do the same thing (though I can’t check their Activity).
My friend tried it from their house, and it does the same thing (no music, no activity on my server) – but it works when they play music from their own library.
Everything else in Plex works fine (the FireTV and Android apps, PlexAmp, etc…), remote access is fine (got my green lock) it’s just the Alexa skill.
Thanks for the report. We pushed a release last week that changed how we handle connection resolution for playback items. Overall it was a large success in unblocking many people from playback. Unfortunately it looks like there are a few edges, including yours, where it broke.
We’ve identified a fix and will be pushing a hotfix to production shortly to address this. Please test in a half hour or later and let me know if you’re able to play music. The first playback attempt will likely lag as we probe your network for a working connection. Subsequent playbacks should start quickly.
EDIT: The release is now live
