Same songs are getting re-synced every time

Thank God I found this thread! THIS FIXED IT!! :-) Summary below. I had the same issue as others did, and spent hours, both with Apple on phone (2 calls), & visiting Genius Bar in the Apple Store (3x)… all wonderful folks, all sincerely baffled by this! We tried all the various “fixes” short of wiping my hard drive!

So, just to give my personal summary to newbies with this issue:

1. Go to iTunes > View > Show View Options (Command+J)
2. Under Music, click Movement Name, Movement Number, and Work.
3. Notice in your Library those 3 new categories showing there now. Chances are you’ll see entries in the Work column. Click on Work, and it’ll group those filled-in fields together. If you’re curious, select all those filled-in-field songs (click on the first; scroll down & shift-click on the last, to select everything in between), & at the bottom of the window it’ll show you how many items you’ve selected; chances are this number will roughly equate with the number of songs that have been re-syncing over and over.
4. Now, with all those songs still selected, go to Edit > Get Info (Command + I). Check the “Use work and movement” box at the top. The “work” field will likely show in grey “Mixed”. In that field, hit the spacebar once, then backspace, to blank out the field. Click OK at bottom right. Now wait… when done processing, your Library should show nothing under the Work column.
5. Now de-select the “Use work and movement” box at the top. Wait… when done processing, sync again. Wait… it MAY take awhile.
6. Finally, sync again. Hold your breath… whew! Worked for me! 🙂

You can still use the Grouping field. I've cleared out the info Itunes added to the Work field to get it to stop re-syncing the same songs, but I still have my Grouping info. The only problem is that Itunes copies the Grouping info back into the Work field again if you make other changes, and then those song will re-sync every time again, until you clear out the Work field again. It's ridiculous.

For now, I created a smart playlist where Work is not blank. Every time a bunch of songs start resyncing - which is every couple of days lately - I go into that playlist, click on the Work field of each song individually to clear the info.

I had three songs that would not allow me to change or clear the Work field on them. I think it's because they were aac audio files. After I created mp3 copies and deleted the aac copies, I could clear out the Work fields on them and they stopped re-syncing.

Even if Itunes assumes we want the Grouping info in the Work field, why should that make it copy the same songs every time you sync? That's totally glitchy.

adding my voice on this problem: I also used grouping to sort DJ mixes, and my phone was (with the most recent iTunes update to 12.5) constantly re-syncing the same 76 tracks—all DJ mixes sorted as such.

I selected "use work & movement" for everything in my library, cleared out those fields, and also cleared out the grouping field.

then i selected everything in my library and de-selected "use work & movement."

presto:no more constant re-syncing.

You are the best.... Me, being such an experienced iTunes User, I was NOT able to track it.....
WORK AND MOVEMENT caused this issue ("work" and "grouping" field were differing)..... OMG... "WORK" not even modifiable for AIFFs, at least in iTunes 12.5.
LET ME ADD, that I first had the problem with only some 80 AIFF files....
within one week, it expanded to all mp3s with id3tag v 2.4 (750 songs). For these ones no problem (convert id3tags back to v2.3 within iTunes).

Addition to the problem is, that id3Tag 2.4 on mp3s can still not be handled by my ipod(s) classic, neither by the one with software 2.0.4 nor the one with 2.0.5. But this problem is only there for several years now... ("lyrics available, but canNOT be retrieved"....)

My solution finally was to remove the "WORK" field (CONTENTGROUP) completely with an external TAG editor (mp3tag.app) from the AIFF files - Any other options, losing my last played dates and whatever else, wouldn't have been an option for me....
Cheers..... YOU MADE MY NIGHT.... Thanks so much....

RIP Steve Jobs.....

Sorry for the somewhat useless post/bump, but I was also having this issue with almost 4,000(!) songs on my iPod Classic, and it was driving me insane. I use the grouping tag for artists who have been in multiple bands or produced/played with other artists, so I can easily make smart playlists that include all of their various projects. Clearing the "work" tag fixed it for me, too. What an unbelievable relief!

It's an annoying bug that adds yet another extra step to getting things to work properly in iTunes, but at least now I know to check for it any time I add new music or alter the grouping tag. Thank you everyone, this was extremely irritating and frequently stopped me from adding new music to my iPod unless I really needed it on there (and sometimes even when I did).

Now if Apple could fix it, that'd really be something. 😝

If you have it set to Sync Music (using automatic syncing), I would go to iPhone's Music settings screen in iTunes and uncheck Sync Music. Apply change. Use iPhone to confirm all songs are removed from iPhone. If there are songs remaining for some reason, go iPhone's onboard Settings -> General -> Storage & iCloud Usage -> Manage Storage (under Storage) -> Music. Remove any songs still on iPhone there.

Then, go back to iPhone's Music settings screen in iTunes and checkmark Sync Music. Set it to sync songs like before. And Apply change. Hopefully, the problem no longer occurs.

I think there's some type of corruption in the database that keeps track of songs on the iPhone. As an iPhone user, you must be prepared to do a complete Restore (Erase) if necessary. I'm "only" suggesting (at this point) you remove your music library, confirm all songs are gone, and sync them back. it may take a while, but you can start it when you go to sleep. Be sure to use a direct USB connection (not WiFi) for that sync, because it's faster.

It's also possible that the problem is on the iTunes library side of the sync, since doing something to your music library made the problem worse. If you don't use the built-in Time Machine feature to backup your system and user data automatically to an external drive, you should (or use some other backup method). Then, run Disk Utility and select your startup disk (usually called Macintosh HD) in the sidebar, and run First Aid to check for data corruption.

I also re-installed a fresh copy of iTunes, but that didn't help either.

It's probably not a problem with iTunes.

I have two problems with iTunes 12.5.3.17:

1. The first, less vexing issue is that iTunes no longer seems to recognize the "Grouping" id3 tag. When I modify MP3 files using a third-party MP3 tag editor, iTunes no longer recognizes the "Grouping" tag and will leave it blank when I import the files into iTunes. Never used to be a problem. Now I have to manually add that tag in iTunes whenever I import new files.

2. The second, and more bothersome problem is the same one on this thread. I decided to add my two cents and more specific details. Every time I plug my iPod Nano (7th Gen) into my computer to sync it with iTunes, it syncs the same 84 songs every single time. The common thread between these songs is that they are all on a smart playlist which contains all my 5-star rated songs (2,175 of them). Some of the 84 have been played others have not, and they seem to be limited to a handful of different artists.

All the 5-star rated songs on specific albums by specific artists are affected, but not all albums by specific artists are affected, if that makes sense. As an example, if an artist has 5 albums, all the 5-star songs on 3 of those albums will be constantly synced, the 5-star songs on the other 2 albums will not be.

Steps I have tried to fix the issue:

1. Someone on another thread suggested it might be due to the new custom lyrics feature. I don't have lyrics on my songs, but I ran a VBS script to strip lyrics from all songs anyways, to no avail.

2. I have also removed the offending songs from iTunes altogether and re-added them, to no avail.

3. I deleted my smart playlist and recreated it, to no avail.

4. Did a factory reset/erase of my iPod Nano, to no avail.

Not really sure what else to try as this issue never happened prior to iTunes 12.5.

Regarding your grouping problem I had the EXACT same problem. I've figured out where they went. If you select a single song and Get Info you will see little arrows next to the Song field. You can select them and choose Work and you will see your Grouping information. It's something they've done for classical stuff.

Quite annoying

Regarding the continuous resyncing problem, I don't think it's a problem with your phone/nano because I have two devices and it's the same problem on BOTH devices.

For me, I noticed that any song on my external drive resyncs but anything local to the machine, on its drive, does NOT resync.

I am going to try editing a local file and see if that causes it to resync over and over. But I'm pretty sure it's an iTunes problem.

Amazing, it worked! Thanks so much to you and @risserfamily.

That does work. The problem is, it works as long as that "work" field (old grouping field) is blank. If you re-add a value, your songs resync again. In fact, I've tried the entire variety of possibilities, and it just boils down to, if there's a value in that Old-Grouping-New-Work field, it resyncs every time. If it's blank, it doesn't.

The good news, I think, is that that means that anyone who is using this feature for classical music will have the same problem, so hopefully Apple will deign to fix it.

But if you are relying on that Old-Grouping-New-Work field to convey information from a third party MP3 editor (like JackPanama and I do), you're screwed until then.