Why Does Itunes Sync Keep Copying the Music Over and Over Again

November 18th update: My sync issues returned, just due to a different cause this time. Details in this post.

After complaining to Tim Cook, and separately starting a (now closed) support ticket, it appears that my iOS/iTunes sync nightmare has finally come to an end!

I accept not seen a progress bar that busy since the day I brought my iPhone 6 back habitation. Any I tried, iTunes simply would not sync everything in my library. In the end, the problem turned out to be as simple—but every bit deadly—every bit this:

In the electric current version of iTunes/iOS, there's a bug that simply appears when you have duplicates of purchased songs. When encountered, a indistinguishable of a purchased song volition (almost always) cause iTunes to silently stop syncing.

This is a known-to-Apple tree issue, and it volition be fixed in a forthcoming update. I'm adequately certain it'south an iTunes issues, but as Apple didn't clearly state which it was, I'm calling it iTunes/iOS. Either mode, until information technology'southward fixed, it'due south a actually bad bug.

Hither's what happens: If you have duplicates of purchased songs, iTunes but silently stops syncing when it hits one of those duplicates. From your perspective, it will expect like everything is working—iTunes never throws an error, and it proceeds through all six (or seven or whatever) steps of the sync process, as seen in the condition window of iTunes.

But behind the scenes, nothing is happening—at least, zilch relative to syncing your files. Equally seen by my troubles, this can be incredibly frustrating and hard to set up.

Continue reading to come across how I was able to finally (with Apple's assist) get my devices syncing again—the catchy part is finding all the duplicates, because they're not all obvious. Likewise note that if you are not having sync issues, I wouldn't worry most duplicates—no demand to endanger what'south already working well!

The "tell"

If y'all're affected by this bug, you'll detect that your iOS device will get some, but not all, of your content. When you await at the device in iTunes, you'll run into something like this:

Those items with the gray dotted circle didn't really sync—iTunes told the iOS device the files were coming (and so they show up in the list), but the file itself didn't transfer. What seems to happen is that iTunes volition sync up until it hits a duplicate of a purchased vocal, so it just stops (without telling yous information technology stopped).

The fix

To gear up the trouble, you have to get rid of the duplicates—note that it's only duplicates of purchased songs that crusade the problem. In theory, this should exist as simple as selecting your Music library, then using View > Show Duplicates. I did that kickoff, and went through the listing of matches to notice actual duplicates of purchased songs.

I found a few, and removed them, but sync still wouldn't work. Eventually, iTunes wasn't reporting any duplicates, so I was somewhat stuck. I'd then send my sync log files back to Apple tree (they had me install a logging profile), and they'd be able to place the side by side song that acquired the problem. I'd remove that one, so we'd and so repeat this process, one painfully dull song file at a time. Ugh.

Why didn't iTunes see these duplicates? Because they're just dissimilar enough to not run into iTunes' criteria, it seems. For example, here'southward a duplicate that Apple identified which passed iTunes' filters:

As you can encounter, the creative person and time are identical, simply the championship and album are not. Listening to each runway, though, they sounded identical to my ear. When you look at the Get Info window for these songs, you can meet some other differences (click to zoom, broad window required!):

Notice that the file sizes are slightly different, and that one item has a purchase date while the other does not. These differences are enough that iTunes doesn't think these files are duplicates, only are shut enough to trigger the nasty problems.

The tool

Then how practise you find these devious semi-duplicates, if iTunes won't identify them? I turned to Dupin ($15), Doug Adams' fantabulous duplicate finder. I tried various combinations of Criteria settings to make sure I was getting all the dupes; this one was particularly effective:

By searching on identical album, artist and rails numbers, I could notice all those duplicates that had different vocal titles (the first three songs above, for instance, all have illegitimate dupes). Not everything found would be a true "bad" duplicate, as some CDs are only weird. You can even see that in the screenshot—Counting Crows' Holiday in Spain and Paved Paradise are both runway number xiii on Hard Candy.

Instead of using Dupin to remove the dupes (which it tin can do), I just switched back to iTunes and decided which one to keep and which one to delete.

After I completed this process—I institute virtually 20 such files, all much older purchases—I was able to sync my iPhone and go 100% of my content transferred—hooray!

A very important heads upward

When you first connect your iOS device later clearing your duplicates, y'all may see this dialog:

If you run into this dialog, it's really important that you click the Don't Transfer button! If you do transfer the purchases back, you'll exist recreating your duplicates. And that would not be a good matter to do. (Ideally, you lot'll accept transferred whatsoever other legit purchases prior to clearing out duplicates, otherwise you'll need to redownload them.)

So how'd information technology happen?

Just where did the duplicates come from? That's a great question, and one I tin can't completely answer. Every indistinguishable I found was a very old iTunes buy—most from 2003, none newer than 2009. I don't use iTunes Match, so it couldn't have been some automatic thing that merely happened. And all the duplicates have notable changes—some have a higher bit rate, some are DRM free vs. protected, some are longer in elapsing, etc.

It appears to me that, somehow at some bespeak in time, I must have told iTunes to upgrade my drove (perhaps related to the removal of DRM, many years ago?). Those new versions should have replaced the onetime versions, but for whatever reason, they did not.

Years pass, and there's no problem, considering this issues is apparently a recent arrival. But once the "bugged" version of iTunes was on my Mac, the duplicate songs became sync killers.

Wrapping it all up

This was a long painful procedure—it's only been iv days since I picked up my iPhone, only solving the sync issue is nearly all I've been doing since then. I thank Apple for the prompt response to my consequence, and for working with me to become everything working again. Everyone was incredibly professional and seemed genuinely interested in solving the trouble—fifty-fifty on a Sunday morning.

Apple'due south "normal" tech support folks were as well very skillful, even if they didn't seem to have the knowledge to solve the problem. They spent quite a bit of fourth dimension with me, making sure they understood the problem. They checked in with me yesterday, to let me know they were still working on it.

Regardless of who solved it, I'grand simply very happy information technology's solved…and hopefully this article volition assist someone else out of the same situation.

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Source: https://robservatory.com/a-nasty-little-itunesios-bug-may-be-causing-media-sync-issues/comment-page-2/