Thanks for replying Drespar! I will certainly add that first bit in the suggestions forums :) Not sure yet on how it performs in a brand new game, but I will create a test one to see how it does and report back. I can say that the playlist contains all songs I've uploaded. Nothing from Incompetech or Tabletop Audio. Another item of note, not sure if it matters, when I noticed the issue, another track was playing simutaneously in the background. A SFX track that I uploaded, again, not from Tabletop Audio. I'll test it again in Chrome and Firefox to see if it's a browser-specific issue as well. Also, for fun, I'm testing it from a completely different machine than I normally use Roll20 on just to see if it's me. :D Thank you again! I'll let you know what my tests yield! EDIT: Tested on the latest version of Chrome on a different computer and with all conditions being the same, it worked as expected, looped just fine. Going to check the version of chrome I had on the other machine where the glitch happened and see if the don't match up. I even tested using the new skip to next buttons in the playback functions and it still looped as expected. Here's hoping it was just a fluke! :D Drespar said: Hey Alnryn, Regarding the first half of your post, that would make a great suggestion over in the Suggestion and Ideas forum! :) As for the second section-- Does there seem to be any dependence on the number of songs that causes the behavior? Are these all uploaded songs or are they from a provided source such as Tabletop Audio? Does this only occur in a single game or can you reproduce it easily in a brand new game? Thanks!