iPhone won't download entire playlist for offline playback on iOS 8.4

Experiencing the exact same things as you. Trying to sync all my music (4400 songs) in a single playlist, and it's just not having it at all. Also a ton of error popups, freezes, crashes, restarts, just like you said.

I don't think it's isolated to a single playlist though, I think the whole offline service is messed up. I'm currently having issues syncing even a playlist with only 25 songs. It chokes and freezes when it gets to "Downloading 3 songs".

This is very disappointing, as reliable offline syncing is probably my #1 must-have in a streaming music service. I'll be going back to Spotify at the end of the trial if this isn't resolved.

Additionally, Apple Music doesn't seem to recognize when playlists made available offline need to be updated. For example - I created a new playlist, added 10 songs, and then marked that playlist for available offline. It synced the 10 songs successfully. However, then I add 10 more and it never recognizes that it needs to sync those. The only way for it to pick up the changes is to hit "Remove Downloads" on the playlist (thereby removing all my offline download progress) , and then "Make Available Offline" again. This is unacceptable.

I can't seem to save a playlist as offline without first going to My Music and saving the individual tracks that are in the playlist. Rather inconvenient. Spotify makes it's simple to save a Playlist for Offline directly from the playlist, not by having to go to a different music tab.

I've only played around with small playlists, because I'm afraid a big playlist would run into issues, but so far I've found that when I make a playlist available offline I can go to iTunes, add more songs to it, and my device will start downloading those songs. However, I did have to restore my phone from a backup before Apple Music would work right (or somewhat right).

I too share all of these problems. One error message I continually get is that I can't download a song because it wasn't purchased with my iTunes account. When that happens, it completely removes every song that it had just downloaded leaving me with nothing but frustration and wasted time. Also, this iCloud Music Library doesn't include music that I didn't purchase on iTunes, leaving me with no way to listen to anything not on the iTunes store at all. These are two major issues that are quickly ensuring that I go back to Spotify, which is far from perfect itself.

Same here, happened after I deleted everything and tried to reload it.

Apple Music filled up my phone (getting a 128GB one next time). All of a sudden, after 8.4, I lost the last several GB of space.

So I'll share my little trick here: I made a smart playlist by size, consisting of 15 GB of my most recently listened to music. I'm trying to sync this, and then some key playlists.

I'm just lost in a flurry of stuck downloads and "Unable to download song" dialogs.

It seems like we're all in similar boats here.

I'm wondering, what if I synced all my local music from iTunes on my computer to my iPhone and then started adding Apple cloud music to my library and making it available offline? As Apple Music just came out, I haven't added many of its songs to my library yet. My iPhone currently has no local songs on it though, just streaming my library from the cloud. Do you think if I synced my music from iTunes I could then just start adding more stuff from Apple's catalog?

I'm just worried iTunes syncing and the new cloud library don't play well together.

Any thoughts?

"I'm just worried iTunes syncing and the new cloud library don't play well together."

You're right, they don't at all. You can only have 1 or the other enabled at a time. Either you sync songs from iTunes and iCloud Library gets turned off. Or iCloud Library on, and no syncing songs. Tried this yesterday.

Okay, thanks for the tip. I won't bother trying, because I don't want to deal with the headache.

Yeah i originally tried that. then flipped icloud back on and did Merge libraries... yeah that didnt work either... i'm not happy, if this isnt fixed in the trial im going right back to Google Play All Access

Oh boy what a nightmare. This is just one of the problems I'm having with Apple Music. I spent a whole day manually adding 1300 songs from my Spotify account. Now when everything is done, can't download the whole playlist. Gets stuck on the last 20 songs out of 1300.