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.
Best Answer
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.