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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 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 at 16:30
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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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