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 18.104.22.168, it's over a USB 3 to Lightning cable.