Music Playlist Continually Fails To Load Next Song

Plex Players
1

Server Version#: 1.40.1.8227
Player Version#: 4.125.1

When listening to a playlist with plex-web, it will play individual songs fine, but it seems like there’s about a 50/50 chance that it will encounter a network failure when it plays the next song - s1001. But, if I hit “retry”, wait about 30-60 seconds, and try to play the “failed” song again, it will play just fine.

I see the issue playing songs locally or remotely. I am listening in random (not sure if that might be an issue). And I see the problem hitting “app.plex.tv” and hitting my server directly - “server.name.local:32400”.
I see the problem using Chrome on Windows 10 or Chromium on a Raspberry Pi.

Most of the songs are wma, and as I mentioned, play just fine directly, it seems to be only when going through a playlist, that it just fails to get the next item.

2

I should add that another odd behavior is that it seems to try to load the next song almost at the end. Kind of like it wants to start playing the next song at the time code of where the previous song ended?