Those of us who like bands that transition seamlessly form one song to the next would love the ability to randomize a playlist, but it always separates those multi-song connected sections. It would be wonderful if there was a way to check a box or something next to songs in a playlist to tell Plex to always play these specific songs in this order, or always shuffle these connected songs together.
What you’re asking for is called “gapless” playback.
Or in a advanced form, Plex calls it “Sweet Fades’”, but it’s actually just “overlapping” of song ends and intros.
There is already an existing feature request for gapless playback, so please put your vote on that.
If you want to experience “sweet fades” right now, get a Plex pass and use either the Android mobile, the iOS Plex app, or plexamp.com (desktop).
Thanks for replying Otto, but what you mention is absolutely not what I’m requesting. I’m fully aware of the options Plex currently has. What I’m asking for is the ability to link songs in a playlist so that when I randomize it, it knows to always keep specific songs together. If I have a playlist of a few hundred songs, I don’t always want that playlist to begin at the top since I’ll never hear the songs at the bottom of the list. This means I’ll usually shuffle that playlist before listening to it. When I do this, because of the shuffe, it separates all the songs that I want to always play together. If there was a way in a playlist to designate songs that should always be connected so when a playlist is shuffled it keeps them together, that would be awesome.
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Then I have misunderstood your request totally. Sorry about that.
No worries. I just know many, many Plex users would love this feature, and it’s not a feature that other programs have. At least none that I know of. It would be a great, “We have this and no one else does.” kind of thing.
Hey Cryptic101 - I’m with you. I have a ton of live recordings of “jam bands” like The Grateful Dead, and there are songs that were designed to flow one into the other, but are technically separate tracks. For example, “Help On The Way” should always be followed by “Slipknot” and “Franklin’s Tower”, because those are really just one long song.
If I could tell Plex “Hey, these three songs are linked; treat them like one track”, that would be stupendous.
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They have no idea how many users would absolutely love this feature, and no other music program has it that I’m aware of. My username came from Cryptical Envelopment btw., part of The Other One. 
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I agree that a lot of users would like this feature. I believe Media Monkey had this feature when I used it years ago already, so it is possible. Songs like Led Zeppelin’s “Heartbreaker” + “Living Loving Maid” or Pink Floyd’s “Another Brick in the Wall (Pt 1)” + “The Happiest Days of out Lives” + " Another Brick in the Wall (Pt 2.)" are just made to be played in sequence.
Came here as another user who would love this feature!
Did you ever get anything sorted?
I think this is very similar to this suggestion:
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For the life of me I don’t understand why this is not a thing!
Artists create albums where they intend the songs to be played together and there are thousands of them.
Even the radio plays them together… most of the time and if they don’t it hurts my head.
The OP was correct, this feature is not available on any other service and I don’t understand why.
Plex could add this simply by adding another field to the DB and when it wants to play one of those songs randomly, it sees the links and plays them in order.
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I could NOT agree more. This needs to be a feature.
I absolutely love the “Library Radio” station and use this as probably 75% of my listening. But there is nothing worse than when Living Loving Maid does NOT follow Heartbreaker.
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voting for this one
This is by far my most desired feature (voted for this a few years ago, was coming back to see if it looked like it was getting enough traction to maybe be implemented)
For what it’s worth, MusicBee, the music player for Windows, has this feature (a few replies mentioned that they’d never run across this kind of feature before)
Yep, +1 on this for me.
