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I keep getting the popup shown below every single time (or almost every single time) I connect my iPhone to my MacBook Pro with a Lightning cable. Every time I click "Transfer" but it always comes up again.

I could click "Do not ask me again," but I do actually want purchased items transferred... I just don't think it's doing that. Any way I can fix this?

I'm not making very many purchases on my iPhone so I know it's not being caused by actual new purchases each time. Also I've tried this with multiple cables so I don't think it's a faulty cable issue.

In case it's relevant I have iTunes Match and do not have Apple Music.

Other details: iPhone 6S, MacOS Mojave, iTunes 12.9.4.94, it's over a USB 3 to Lightning cable.

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  • Many issues related to syncing that may help you here - macworld.co.uk/how-to/mac-software/…. – slm Apr 21 '19 at 15:34
  • I looked a little more closely and the sync does seem to complete, or at least I think so. Also the iPhone is still successfully backing up to the Mac. Looking really closely, one of the items it's trying to sync is a book that is already in iBooks on both the Mac and the iPhone. In fact, there are TWO copies of the book in both locations. There is a minor difference I see (on the iPhone the two book covers are orange and blue, and on the Mac they are both orange). – Stephen Apr 21 '19 at 16:30
  • @slm: Many issues, yes—but none of them have anything to do with this question. The worst part of the problem is the threat that Apple is going to delete things. Let's phrase that another way: "If you don't make another copy of this thing-that-we-won't-tell-you-the-name-of on your computer, you won't have any copies at all." – WGroleau Aug 27 '19 at 16:56
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I was having the same problem. When I looked a little more closely, I found I had checked that I wanted "Selected Books" to be synced. For the three books I had checked as ones to sync, I am now showing multiple copies (10 copies in one case) in the iTunes Books sync page; although there is only one copy of each when I look in the Books app on my iPhone and Mac Mini. Since I have my Books app on the iPhone set to use iCloud anyway, decided there I didn't need to also sync them when I do my iTunes sync. After unchecking "Sync Books" and hitting "Apply" in iTunes, the every-time-I-do-an-iTunes-sync reminder to transfer purchased items have stopped.

Maybe when iTunes gets split up into separate apps (as I heard might/will happen) these iTunes sync issues will get sorted out. But don't get your hopes up. I think we're lucky Apple supports sync-to-your-computer-without-using-iCloud at all.

Other details: iPhone 7, iOS 12.2, MacOS Mojave 10.14.4, iTunes 12.9.4.94, Lightning cable.

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