IOS 8 won't sync music with itunes

Same issue here, 128gb iPhone 6 iOS 8.02. At random times, some or most of my music syncs, but on subsequent syncs, they are no playing on the iPhone (they seems there, but when you play them, it skips through a whole album on leaves the square with red circle symbol.

Most of my music is ripped in iTunes from CD into ALAC, and I am using the convert to 256k option.

Interesting, the only songs that always successfully sync and remain playable on the iPhone are purchases songs...

At times, there is a large disparity between the GB used on the phone as listed in iTunes vs the Memory usage on the phone; other times, they are close (but never exact) Even with the phone seems to have the songs there (as noted by 30+ GB's of files in Memory, playback just skips right through them

If I go to Songs on the iPhone and skip through all the titles to the end, and re-sync, iTunes starts to download all of them again, but after a subsewnt sync, the inability to playback iTunes ripped music reappears

I think I have been temporarily successful.. I synced and resynced with no success. Finally, I synced my iPhone 6 with these two boxes checked: Sync only checked music and videos, and Manually manage music. I had my music choices previously checked before I checked the Manually Manage music box. with this latest sync I got ring tones and music that was on my iPhone 5 before I moved it all to the 6. I am scared to resync after reading all of these posts where everyone has lost their music over and over..... We need an iTunes update quickly, Apple!

I'm experiencing the same issues. I'm using an iPhone 6, 128 GB, running 8.0.2. I'm also running OS 10.9.5 and using iTunes 11.4.

The first time I sync my media everything is fine. When I go to re-sync, everything EXCEPT my "purchased from iTunes" media gets skipped over. There is no indication when syncing that my "non-purchased from iTunes" media is/has been removed. Once I sync after the initial sync everything appears fine but all of those songs get skipped over in a rapid succession until it lands on a track that I have purchased from iTunes. I have done SEVERAL restores including setting up my device as new and NOTHING has worked. I have tried everything on this thread and others, such as checking various options and the like. I have a large iTunes library and I will no longer sync until apple updates iTunes. I will just depend on Spotify until something is worked out. I called Apple Support and they didn't quite understand the issue and instructed me to re-install iTunes after an hour of troubleshooting.

I am at a loss for the time being. It's unfortunate that I have this phone with a great amount of storage now that I cannot use. Hopefully they notice this issue soon.

Make sure EVERYONE goes here:

https://www.apple.com/feedback/iphone.html

and posts the issue with Apple...they will matter more than here.

Wouldn't hurt to post the same on the iTunes feedback portal as well, since its not clear where the problem likes

I did try one thing, and it worked for the first sync - I changed the iTunes library simply by adding a song (fa ree download from iTunes) Everything seemed to sync after that, though I haven't done a second sync to see if it sticks. If it does, perhaps making a change to the library corrects a corruption, but that's just me guessing...and that may not be the fix for everyone...

None of the above solutions worked for me but when I unlocked the phone with the password, they copied straight across, so it's worth checking that isn't the problem if you're having the same issue.

I don't understand this - if I try to sync and my phone isn't locked, a pop up message tells me that I need to unlock my phone.

I haven't read everyone's replies, but enough to try some things. Here is my scenario:

iPhone 5S 64gb works great with iOS 8.0.2, Windows 7 iTunes 11.4.0.18. No recent issues with Podcasts or Playlists. I have regular playlists, Smart Playlists, Smart Playlists that utilize other Smart Playlists.

Got the iPhone 6 128g on Wednesday, set it up, and refreshed from the 5S backup to move apps and settings and content, and it has not been able to consistently handle either Podcasts or Music, syncing or playback. I do not want to factory reset. iPhone 6 is also now at 8.0.2, I did not get the 8.0.1 fiasco on either device. Podcasts go back and forth between being on the device, or showing in the cloud, seemingly at random. Music sometimes syncs from iTunes, recently not updating at all. Music Playback initially was comical: Start a playlist and the iPhone 6 would race through the display of each song, no playback, no registration of a PlayCount, then erase the songs from the device. Often it also would not be able to play a music file. I listen to Audiobook files as well, was listening to one today, it completed and the next one in the group didn't play, would not play, the one just completed was removed from the device, though seemed to update through iCloud to my iTunes that it completed.

I have removed Music, Podcasts, Apps, all that stuff from syncing, to remove it and then click iTunes again to reload it. no change in behavior on the iPhone 6. (meanwhile, the 5S keeps working great, using the same iTunes files, syncing flawlessly, keeping me sane)

I even created a brand new simple Smart Playlist, to see if some "old" playlists were the issue. That new simple Smart Playlist did not update to the iPhone 6 either.

So I just clicked "Manually Manage Music and Videos", for the iPhone 6, after one of the suggestions here. Everything else didn't make a difference, so wth. And it synced!!! All the previously selected Playlists are now synced to the iPhone 6. The Music tab in the iTunes iPhone 6 screen is now blanked, so I can't change the selected playlists apparently, so a new issue results, but at least a sync did occur 🙂 Now we shall see if taking off "Manually Manage" so I can see the playlists again will make any other difference. But I have a basic kludge, sometimes that is all we can ask for.

This is a significant software issue on the iPhone 6. Sending a bug note to https://www.apple.com/feedback/iphone.html

I'm having a very similar problem. iTunes will only allow me to sync 76 of my 832 songs, and the selection is arbitrary. Some of the songs are ones I purchased from iTunes, some songs are from CDs, and some songs are from Bandcamp pages. There doesn't seem to be any rhyme or reason which songs iTunes will sync to my iPod, not even song length, song size, artist, album, or genre.

I've tried all the things people have suggested and nothing's worked. I'm not going to reset my phone to factory settings and manually install all my apps and manually reenter all my contacts for a second time, the first time was enough of a pain.

If anybody has any idea why this is happening, please let me know.

The people suggesting checking "Manually Manage Music and Videos" - I thought either you synced your library or you manually managed it. Is this not the case? I've only ever checked that if I was putting music on a device that I didn't keep in iTunes.

Can you "Manually Manage Music and Videos" if you are syncing your library?

I spent 5 hours at the Genius Bar today and solved this issue. The root cause for me was not having updated my iPhone 5 to iOS 8, AS WELL AS updating all apps to their most recent version. So, I updated my old iPhone 5 via wifi (my new iPhone 6 was already activated), BACKED UP THE IPHONE 5 TO MY COMPUTER. Then, I did a restore on the iPhone 6. All apps, books and photos then automatically synced perfectly, but not my music library. Then, I turned off iTunes Match on my phone, turned the phone off and on, selected "sync all" in iTunes on my MacBook Pro, clicked "apply", let it run until it reset the settings, closed iTunes, and reopened it. The music library (3500 songs) then synced completely without further interruption. The Genius bar tech and I agreed that starting out with an UPDATED backup from my old phone and turning of iTunes Match seemed to be the keys.

Note: My wife had updated her iPhone 4 to iOS 8, as well as all the apps before I upgrade her to the iPhone 6. Her upgrade worked perfectly. I hope this is helpful.

Well, a second sync wiped out my music again (except of iTunes purchases), so my attempt above (changing the iTunes Library by adding a file, which worked on the initial sync) did not persist as a fix.

Errk!: Yes, you are correct, in a logical world that would be the case 🙂 I typically keep the "Manually Manage Music and Videos" NOT checked on my iPhone. I have had to check it On (usually on an iPod Touch) only for audiobooks checked out from the local library that need to get direct access to copy the licensed files to the device. So, no, I did not expect that I would have to change the "Manually Manage..." check box.

This is not a typical situation, so checking this box became the last best hope to try something that would shake up the music connection between iTunes and the iPhone. As noted, it takes away the ability to adjust the Music playlists (and I assume videos) that you had originally checked, but it synced that same set of items anyway. De-selecting the 'Manually Manage...' check box went back to some of the funky syncing activities, so I think I will be going back and forth using "Manually Managed" On in order to sync, then Off in order to make any changes to selected items in Music, then back to On in order to sync those new selections.

And, in general, when you turn on "Manually Manage", it leaves anything on the device that happened to be synced earlier. It is only when you take off the "Manually Managed" that it warns you iTunes is about to overwrite the iPhone with only your Playlist selections. Even then, I've seen files that were manually put on the device remain, and I had to manually delete them on the iPod Touch directly, the Sync would not erase them, or I didn't figure out how to get the sync to erase them.

It's a kludge. And I'm still gun shy about the failures when the iPhone 6 actually plays the music, how it tracks the files, I'm not certain that is solved yet.

Little more testing, and this may be finally working (background: 128 GB iPhone 6, 8.02 mostly ripped CDs/ALAC, some iTunes purchased music)

Note: This cleansing assumes you know where all your music is, which for nearly everyone, is in the iTunes Music folder. If files are not organized and are instead scattered all over your computers and external hard drives, the step requiring deleting and re-adding the files will take quite a bit of hunting and searching)

• With your iPhone connected and selected in iTunes go the Settings > Music in the sidebar
• Check Sync Music if not already checked
• Check Selected Playlists, Artists, Albums and Genres
• Deselect EVERY checkbox below (Playlists, Artists, Genres, Albums) No music should be selected
• Sync (you will be warned about removing music from your iPhone)
• Disconnect your iPhone

You now should have no music on your phone. To check (on your iPhone):

Go to Settings > General > Usage > Manage Storage

and verify that "Music" is not there (or has 0 GB). If there are files still on your phone:

• Select "Music" on the Manage Storage page on the iPhone
• Click Edit
• Click the red minus symbol next to all songs

Next (and be sure recovering from this is easy for you), go to iTunes on your computer and view all your music (Song view is easiest)

• Select ALL the songs in your library (CMD-A) They will be highlighted blue
• Right Click on the list and Select Delete (yes, delete all songs from your iTunes Library)

Read very carefully here:

• You will be asked if you are sure - click DELETE SONGS
• You will be asked if you want to delete the files from your computer. Select KEEP FILES

Once this is done, Quit and Relaunch iTunes

To re-add your Music:

• iTunes > File > Menu > Add to Library
• Navigate and select to your iTunes Music folder (the folder that contains all your music)
• Select Open

iTunes will now start adding back all your Music - this can take several minutes if you have a lot of music

Once it's complete, reconnect your iPhone, and re-enable the Music selections you wish to Sync (either Entire Music Library or Selected Playlists etc...)

Sync

I've done this over a dozen times, adding a few artists at a time, and checking by disconnecting, reconnecting, and syncing before adding more artists. The previously loaded files continue to play correctly after a second or third sync. I've done about 3 gigs of my 30 gigs so far.

Note that is quite likely this might work just doing the last part - deleting and re-adding the music to iTunes. But its not time consuming and helps start with a clean slate by starting as outlined.

Hopefull this continues to work, and works for others.

I'm guessing this forces a cleanup of the iTunes Library file, and re-adding everything rebuilds it. If it recurs, I'm out of ideas short of restoring as a new phone.

Good set of instructions, Greg. Do the Playlists remain as is, and rebuild the songs which were originally in them? Are the Ratings maintained for each of the song files?

Thanks

Playlists are unaffected; rating I don't know as I don't use them.