Been in touch with nearly 10 Apple specialists since 9/29/14. For much of this time, I've been volleyed between iTunes and iphone specialists who felt that my issues needed to be dealt with iPhone specialists or vice-versa. My music problems started immediately after syncing my new, 128 gb iphone 6 on that date. I've spent hours and hours and hours and sleepless nights spent trying to figure this out (I have over 10k songs) while they often have taken control of my computer and had me delete this, re-install that, restore this, update that... They've also uploaded some files from my computer to their engineers. Here's what I've noticed...
- If I do a factory Restore of the iphone, all songs seem to play fine. No, I don't play them all, just skip through a hundred or so.
- As soon as I do a subsequent sync, any songs that were ripped from CD's or purchased elsewhere (Amazon, etc.), do not play.
- The Music app immediately skips over these songs and flips through subsequent songs until it lands on an iTunes-purchased song and plays those only.
- When I return to the song list, the non-itunes-purchased songs I tried to play become greyed-out and have a red circle with a red square to the right of each one.
- After a subsequent sync, those greyed-out songs disappear entirely from the song list.
Similar to the above, I've unchecked Sync Music after connecting my phone. As with all syncs after disappearing songs, the iTunes status "Waiting for changes to be applied" remains for a loooooong time. Eventually, sometimes after hours, I will stop the sync process (clicking on X), eject the phone and find less songs on it. From this point forward, nothing via iTunes will remove the songs (sometimes still thousands) remaining on the phone.
After weeks and several different Apple specialists, the most recent suggestion they've offered me is to update all desk/laptops to Yosemite (which I've done), update all mobile devices to iOS 8.02 (which I've done) and turn off iTunes Match on all desk/laptops and mobile devices (which I've done). Apple engineers maintained that the issue had something to do with needing to update to Yosemite. Well, my latest syncs today confirm that they are dead wrong. The songs still become greyed-out and go missing! NOTE: I did not upgrade/use iCloud Drive until *after* I just upgraded to Yosemite.
Instead of doing a complete restore for the umpteenth time, I just tried, for the 10th(?) time to delete the tracks directly on my phone:
Settings --> General --> Usage --> Manage Storage --> Music --> Edit --> delete button (or slide and select Delete)
However, the Settings app just crashed (as it usually has) after I press Delete. I scroll through all of the Stored apps and spend several minutes looking for the Music app's storage, but do not find it. I reconnect to iTunes and what remains is 1-2 songs that were last played on the phone. Can't erase it/them.
It just seems like there might be a dbase on the phone that is screwed up or not getting updated or something. I continue to question the Apple folks about this. Also if there's an issue with iTunes corruption or the manner in which iTunes communicates with and controls updates (adding/removing songs) during the sync process. If I'm correct, it **must've been** caused by one or more of the following: iTunes, iOS, iOS Music app and/or the sync process because I had zero problems with my previous iphone 5S and the exact same other desk/laptop and mobile devices.
So, if I want all of my music back on the iphone, the ONLY WAY is to do a complete restore, which takes HOURS! And then I am 100% unable to add more music unless I perform another complete restore!!
The suggestion that I recently proposed to Apple was to give me an iTunes gift certificate that will allow me to purchase all my non-itunes-purchased music through iTunes. Should only cost them a few thousand dollars. No answer from them yet as to whether they'll do this. Somehow, I'm skeptical. If they can't fix this, I'm going to start posting this to every site I can to find others suffering with this issue and drum up as much support to yell and scream until their so-called "engineers" get moving and fix it. I have zero faith in allowing Apple to handle my payments with Apple Pay if they're unable to fix their oldest mobile offering (playing music!!) for many of their money-paying customers. What the...?!?!