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

**Bump**

Alright so it seems I've stumbled upon a solution to downloading big libraries for offline use. I discovered it while I was organizing my library with smart playlists. In my experience it seems that problems tend to arise when you try downloading a lot of songs from only one playlist. After several hundred songs there are errors and sometimes downloading completely stops (usually after 2k). Also the offline badge may disappear on your playlist which causes all downloaded songs up to this point to be deleted on the next reboot. Given these insights it seems apple didn't optimize the software enough to handle large playlist offline requests. Until they do, the only way to get all your music on your device is to break your library into smaller chunks, download those playlist one by one for offline use and it should be smooth sailing once you got all your music on your device. The best way to do this is to use smart playlists to auto separate your music (and auto download new songs). Now there are many ways to do this and a lot of its up to personal preference. I kept it simply with two folders. Owned music (folder 1) and apple music (folder 2). I then made the following smart playlists:

Folder 1

Albums (CD Owned)

I got all my full albums together in a regular playlist (ones that I have physical copies of), selected all the tracks, hit get info and then in the comment section put "Entire Album (CD Owned)". After that I created a smart playlist with the following rules: Media kind is music, Comments is "Entire Album (CD Owned)" & iCloud Status is not Apple music.

Albums (Digital Copy Owned)

Same as above however it was music that I only had a digital copy off. Just replace "Entire Album (CD Owned)" with "Entire Album (Digitally Owned)".

Solo Tracks

Made a smart playlist with the following rules: Media Kind is Music, Comments is not "Entire Album (Digitally Owned)", Comments is not "Entire Album (Digitally Owned)" & iCloud status is not "Apple Music". This created a playlist with songs that are not part of an album that i have all the songs to.

Folder 2

Apple Music Library

I don't have many songs on apple music yet so I just have one playlist with the following rules: Media kind is music, iCloud status is "Apple Music".

Now my 3819 song library is split into smaller playlists (1842, 1351, 626 & 37 respectively). Next I just hit download (make available offline) on one playlist at a time (downloading all the songs on said playlist before i tried moving on to another). However some tracks still hanged up. What i did was wait until all the songs that could download did and all that was left in the download que were frozen songs. Rebooted the iPhone, opened up the music app and the other few songs download like a charm. Repeated until all my music was download.

So basically you want to use smart playlists and the comment sections of songs to break down your library into smaller manageable chunks that your iPhone can handle, then download. Once you do the downloads can go through and any new music will be downloaded automatically. Like I said before how you do this is up to you, i explained how i did it above.

Lets hope that apple can make some positive changes before iOS 9 so that their will be a easy way to download all your music. Making a bunch of smart playlists to do the job is tiresome. Until then this is the only solution I found. Hope it helps out any other music lovers. Thanks!

Did you reboot your phone after all you were left with was your stuck downloads? I had to do it for each playlist. Once I did the phone downloaded the rest no problem.