I have the same issue so I'll see if my info will help Tanner.  Playlist has let's say 350 songs I hit shuffle and within 20-30 songs I'm getting repeats then in the end it never expands outside of a hundred songs max.  Meaning you never get to hear all the music in the playlist and the repeats are at a point annoying.  I would recommend a function adjustment by the dev team that says the random pics only come from the yet to be played/unplayed items on the list as the listening session goes on and it should remember that and randomize/shuffle the remaining songs until the playlist is complete then start shuffling the whole list all over.  We spend a lot of time curating our playlists with songs we love we actually want to hear them all and in a more creative way than listening to them in the same order.   I would love for there to be a shuffle function that says randomize songs not played until it exhausts the playlist.  I've been working in computer development for 6 years I know this isn't a difficult thing to do. Simple logic that would actually shuffle to hear an entire playlist before repeating.   ... View more