Server Version#: 1.16.5.1488
Player Version#: Echo (1st Generation) and the Echo Show (2nd Generation)
According to this list of Alexa Voice Commands, Alexa should be able to loop (repeat) songs on Plex.
While playing a song on my Echo from PMS, I tried saying, “Alexa, tell Plex to loop.” Alexa responds, “Turning loop mode, loop mode: ON.”
When the song is finished it does not play again – it just stops. What is “loop” supposed to do?
I’ve noticed this too. It says it turns on loop mode, but it doesn’t loop. I try to use this in conjunction with a sleep timer, but to no avail since it never loops.
This still isn’t working for me. Seems like this is pretty basic functionality.
Apparently, very few people use looping via the Alexa interface. 
It seems the Plex developers are not very active on their forums… 
I would really like this feature to work as my kids like to listen to stories at bed time but right now the echo is not very useful because it stops at the end of the story even if the echo tells me Plex has turned loop mode on. Come on Plex team!
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