Looking for an exit from the iTunes iPhone Music sync hell by enabling “Sync Music”

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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


  • 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?

This whole thing is so time consuming 🙁

Author: Dhanraj7978

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