Using iTunes (latest) on a Windows 11 laptop and iPhone (iOS 16.2).

I have 4000 songs on the iPhone, and a bit more in the iTunes library (from CDs... ; the lib was manually copied from the Music folder after a PC upgrade, and is correctly shown in iTunes Library).

  • Transfer Purchases (to iTunes) has been done (from my 2 Apple accounts)
  • Not an Apple Music subscriber

---- Target ----

On iTunes, I want to be able to

  • add other CDs
  • listen and remove about 30% of the old songs in the iTunes lib
  • then sync that to iPhone

For that, "Sync Music" (device / settings / Music) is necessary. But a click on the Sync Music gives this message, triggering a few questions

enter image description here


  • How can I see what would be deleted if Sync Music is to be performed?
  • my numerous iPhone playlists are not listed in iTunes, will they be cleared on the iPhone? What can I do to prevent that?
  • no Books is shown in iTunes (have plenty on the iPhone), the message says they will be deleted, why would Sync Music clear the iPhone books? Will that really happen? Can I avoid this?

A simple setup that should not take so much time :(

2 Answers 2


Simply said, any media added directly on the iPhone or synced to it from a different computer than your current one will be deleted. There is no possibility to see the list of impacted files beforehand.

iBooks most likely can be preserved via a login into iCloud on the iPhone and enabling iBook syncing.


Do all of the items on the phone originate from that specific instance of iTunes on that computer?

iTunes is the 'master' in this arrangement, the phone the 'slave'. Anything not already in iTunes on that specific computer will be discarded as it syncs. It does not copy songs/books etc back from the phone, only such as playlists.

  • I'm not sure. Data has been copied along from comp to comp for a decade. And, this is the important point, "Sync Music" is unchecked since an earlier version of iOS (probably when Apple released the Apple Music subscription). So, iTunes is not the master anymore since that time. Each new iPhone had its data from a backup restore, not iTunes data.
    – Déjà vu
    Commented Feb 15, 2023 at 1:38
  • So what you'll have after sync is only the data that currently exists on the computer. Anything on only the phone will be deleted. Playlists should sync, but no 'hard data'.
    – Tetsujin
    Commented Feb 15, 2023 at 7:50
  • Well, that's why there are "questions" in my question. And playlists will sync from the comp to the iPhone, i.e. the iPhone (valid) ones will disappear... As asked in the question, how can I prevent that.
    – Déjà vu
    Commented Feb 15, 2023 at 8:01
  • You can't. As I already explained, iTunes is the master, the phone is the slave. There are 3rd party apps that claim to be able to pull music from the phone to the computer, but I don't use Windows so idk which might be any good. Once in the computer, you can then get them into iTunes.
    – Tetsujin
    Commented Feb 15, 2023 at 8:03
  • The iTunes being master is the target setup, the risks are assumed, thus the question. There are 3 questions 1) How to show diff bw iphone music and itunes lib, 2) "prevent" is not the right word - better is "how to backup the iphone playlists", 3) Books - why would they be deleted? How to backup them ....
    – Déjà vu
    Commented Feb 15, 2023 at 8:14

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