Q: Music Won't Sync From Itunes Correctly

Well, I was overly enthusiastic about the apparent Yosemite fix so I upgraded today and...well now the movies, tv shows AND music are all screwed on all devices. I might try deauthorizing all my devices, and then digging out my old walkman. I still have cassettes of Beatles albums, which is more music than the 2 ipads and iphone 6 currently. Reboot after reboot, erase music on fone, click all buttons in iTunes...my saturday has been a carnival of stupid repetitive actions. For the first time I'm actually beginning to regret buying this now, and that makes me very very sad.

Check out this site.  http://robservatory.com/a-nasty-little-itunesios-bug-may-be-causing-media-sync-i ssues/ A gentleman posted this in a similar thread.  He apparently worked with some apple engineers to get this straight.  I have been dealing with the same issues.  I finally broke down and purchased this tool to clean up my library and I'll be ****, the problem is gone.  I restored my phone one last time last night as iTunes had it so messed up there were songs on it that were not being reported and I had no way to remove them.  I used the "Dupin" tool to eliminate all duplicates from my iTunes library.  It is finally working as it has always done in the past.  I've done several syncs with multiple playlists.  Its finally working.

Very interesting, and in line with my own results, where finding and deleting the duplicates finally solved my problem.

I second this: I also believe my problem was solved by deleting all of the problematic duplicates in the correct manner (as I described in my earlier post).

Very interesting find! I went to try it, but it is a Mac application (I'm currently running on a PC, but I did duplicate the issue on my mac, so I'm assuming it is a problem with my library). Using iTunes to identify duplicates was pointless for me, as it found 3500 duplicates, and most of them aren't truly "duplicates". For instance, I have 3 copies of one song: 1 from an album, 1 from the artist's live album, and 1 from a live recording I made at a show. They are all different lengths (3:58, 4:33, and 5:34) and reside in different directories. None were purchased from iTunes. Yet, each of the three are among the songs that become unplayable upon subsequent syncs.

Going through 3k songs to figure out what the troublesome track is does not really seem feasible at this time. I'll keep searching for a Windows version of a de-dupe program.

Yep those wouldn't cause the bug.  The duper program allows you to scan for duplicate files with some pretty good options.  I was able to weed out most of the offenders filtering files by name and time.  That got the true duplicate items such as the same song from say an original album and greatest hits.  It definitely fixed the issue.  I've got all my music organized now and I've done several syncs without a single issue.  Now apple needs to fix it, half the reason I had most of these duplicate files was due to iTunes downloading different versions of songs to my library over the years.

Has anyone updated to iTunes 12.01? If so have they tried fixing this?

Okay I have updated to 12.01 (and deleted all purchased songs) and the problem still exist. Can't believe Apple hasn't fixed this yet. Yet they find time changing the iTunes icon from blue to red.

I have been using Google's Play Music to listen to new songs...

****.

mine worked finally after a month of trying, basically i turned iTunes match off from the device, plugged my device (Iphon6 128gb) via cable to my PC, launched I Tunes, on the summary page automatically sync when this iphone is connected checked,  sync only checked songs and videos checked only, apply, sync, then my songs started to load all of them, made duplicates of some playlists after the transfer which i had to delete. i did couple of syncs after that it was ok, and i made new playlist also and synced, transferred normally.

Well, I played with a couple of de-duper programs, and removed about 60 or so tracks from my library. Like you, they were duplicates because it was the same song on a different album. Very unhappy about doing it, but this is temporary. I've backed them up to another folder and will restore them once I get the apple fix.

Now, I no longer get the missing songs, but I am getting a whole slew of new sync issues. I take different problems as a good sign, because this mess of iTunes 12/iOS8 is an onion with several layers of issues, each one more stinky.

My new issues are:

- some songs just don't copy over. I have one playlist that is 371 songs. Yet only 369 songs make it to the phone. No idea why the other 2 didn't copy.

- playlists are now all alphabetized by artist, instead of in the order I had them in iTunes. Super annoying.

- subsequent syncs have made the artwork disappear. Very odd, since I have embedded all my album artwork into the mp3 tags. This is obviously an iOS issue, where the other issues may be iTunes.

- The "waiting for changes to be applied" hangup is back. Hadn't experienced that on this phone yet. Now I have a 50/50 chance of needing to cancel the sync and restart when I see this.

So weird that none of this happened until after I deleted a couple of songs.

What's going on, Apple?

Thought I'd share one thing I found that helped me identify which dupes were causing the problem, in case you didn't want to shell out $15 for the program linked above (or like me, are on a Windows box and can't run it).

First thing I did was identify all the duplicates from the iTunes store (the quickest way for me was to add the field "Purchase Date" in iTunes). Out of 3500+ tracks that iTunes considered "exact duplicates", this was about 60 tracks. I removed them from the library and moved them to a different directory on my computer.

Next thing I did was have to restore a cloud backup (unrelated to this issue. All my audio files turned to "other" and I didn't want to spend time deleting it, so I reverted to a backup I did to the iCloud last night). After I did a restore to my backup, I connected to iTunes to start to transfer music. I saw three songs get copied to my iTunes library - this was weird, because I never got the popup asking me if I wanted to transfer purchased from my phone to my library. Through trial and error, I have identified that these were the only 3 tracks that were causing my issue. In subsequent syncs, the iPhone kept sucking them down and putting them into my library, even though I have disabled match, show all songs, iCloud, and every imaginable setting on the iPhone. Frustrated that this kept happening, I factory restored and setup my phone as a new phone. I made sure the 3 culprits were not in iTunes, and the problem is gone - all cloud based settings are disabled and the phone is no longer attempting to grab these tracks from the iTunes store.

Struggling to find some common thread of what caused this, all 3 of my "bad" iTunes songs came from free downloads I got from the weekly cards they have at Starbucks, all circa 2011. Not sure if that is a coincidence or not, but I won't be taking any freebies from the iTunes store anymore.

It has now been 30 days with my new phone and I am finally able to use it. While I am happy there is a solution, this whole experience has soured me on Apple. Really unsatisfactory that the people on this thread and other sites had to brainstorm for acceptable workarounds while there is silence out of Cupertino.

and? does 8.1 fix it? i am gonna scream if it doesnt

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