Just adding to the list of people whom have the skill setup and working. Commands properly go though, midplay pickup happens properly being asked if I want to pickup where I left off. But Alexa still follows up with an Uh oh message.
To add some additional information… Easter Eggs are not coming though. Movies like Die Hard and Super Troopers will start playing, but I get an Uh oh reply instead of the expected Easter eggs.
I’m getting the error with every possible command then it “attempts” to play but get hit with a visible “cannot be played” message with just the retry or close options, the media works fine via any other method other than alexa, tried singing in/out, re-auth, restarting server/echo etc with 3rd gen dot - it used to work around this time last year with my 2nd gen dot but then it just became unusable and only recently got another dot so thought I’d try it again.
it literally provides no function for me other than being able to find servers / players - beyond that I can’t play anything
I keep getting the “your plex server (pause) is offline”, despite it clearly being online. This time even multiple restarts won’t help. Plex keeps telling me there’s an update as well, but as usual the repo’s are lagging behind. Not sure if that’s related.
Don’t know if this update will be of any help; But I would like share my findings.
I am connected to Amazon Germany using Plex Server 1.16.2.1321.
Had the same annoying error msg. with the Plex Skill.
For me It looks like the root cause was that my server was not able to establish a secure connection. (https://support.plex.tv/articles/206225077-how-to-use-secure-server-connections/)
I configured port-forwarding and I was able to connect via WAN-IP to the server. But connecting remotely to the platform it did showed: “can establish”… “use insecure?”… and I accepted. Since than, I had the red symbol near the server name.
As far as I remember, I removed the server from the environment list and from the “allowed devices”. Furthermore, I did a reboot of the server and connected the Plex server back to my account.
Now the server is providing me with a secure connection and Alexa Skill is working as expected.
Changing it to a “secure connection”, disabling the skill, removing authentication, restarting the server then enabling the skill and authorising again after still didn’t work for me
Thankyou! this worked. Was driving me absolutely nuts
What did you do to get it to work, as I say above I’ve tried what has been outlined in the posts here and I’m still getting no luck, it’s doing my head in 
I am having the same issue. I set it up on a Roku and it works great except Alexa always tell me the uh-oh message. Plex team let me know if I can send you anything to figure this out. The features are great but now she’s just annoying
I don’t know if this will help anyone (or if it’s already listed in the many comments…)
I FINALLY got this to work by enabling Remote Access. Even though Alexa could connect to my server and allow me to switch servers, it would give me the “uh-oh” message for playing music (or anything else besides changing servers,) until I enabled Remote Access.
Remote access is (and has been for ages) enabled, port forwarded and still no dice
@vanstinator, I am also having the issue with an Echo dot gen 2, PMS 1.16.3.1433. Oddly enough, when I asked to play a movie it recognized I was in the middle of it, it gave me a visual error on my Plex Media Player (windows) but I had the web client open on my desktop (chrome) and it seemed to start playing there even though the error was on my PMP. When I try to set the default player to my PMP, Alexa also gives me the “Uh oh, something went wrong, I’ve alerted the Plex team”.
I too used this pretty frequently and it’s only recently stopped working.
Another +1 for it not working here (UK), like others above a) used to work fairly well until recently, b) have tried the usual remove/re-add both the Alexa ‘skill’ and related ‘authorised device’, c) while there is obviously some sort of connection (eg. it can read out what’s on deck) I get the “uh-oh” message to pretty much every request.
Can’t understand how this remains broken for so long now (weeks/months even?). Please fix!
Broken for me too. Has been for months. Clearly the devs could give a sh*t. Its been broken for months. Glad I have a lifetime plex pass for them to never fix anything. If the skill doesn’t work, remove it from the store. Im blown away by how long its been broken. I used it all the time. How embarassing.
I also had these problems, but has been behaving on all my Alexas for at least a couple of months.
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I have the Emby version of the skill working, too. Always good to have a backup. I use Plex for playlists, and Emby to get a deeper dive into my music collection. (The two seem to “randomize” differently.)
I’m having a related issue with the “uh oh…” prompt, but with one significant difference: The voice commands work for me. For example if I tell plex to pause or stop playback on my default playback device (in my case it’s openPHT), it works just fine. My main issue is that Alexa still says “uh oh, something went wrong…” even as it successfully executes the desired command. I tried disabling the plex skill from Amazon, and re-enabling it after removing Amazon Alexa as an authorized device in my plex server.
The plex skill links itself as an authorized device just fine after re-enabling the Amazon Plex skill, but the original problem doesn’t go away, and so Alexa still proceeds with “uh oh” even though it correctly executes the command. This is irritating, as I don’t want to hear repeated prompts from Alexa that are made in error. Someone please help me disable this “uh oh” prompt, since Alexa is wrong about this anyway. Thanks!
Starting yesterday, Plex on Alexa started getting flaky. Then got only the “trouble accessing your Plex skill” and “uh oh” messages. Disabling/re-enabling, rebooting, deleting auth device of Alexa in Plex/reauthorizing did no good. Still have Remote Access enabled. Plex is up to date.
Emby Alexa skill still working fine.
Same here. Playing music from Plex through my Echo had been working just fine for months, then out of the blue yesterday it just started failing. Similar attempts to fix (disable, reboot, re-auth, etc.). No dice.
Stopped working for me yesterday after the latest Plex update (v 1.18.1.1973); now just “uh-oh, something went wrong…” message. Beyond frustrating!
