iPhone 14 won’t sync with late 2015 iMac.

I upgraded from iPhone XR to iPhone 14. Sync always stops at “determining items to sync.” Just keeps churning. Won’t sync on other accounts either. My wife’s iphone SE will sync on all accounts. Photos won’t load for importing either.

iPhone 14

Posted on Mar 15, 2023 7:28 PM

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Question marked as Top-ranking reply

Posted on Mar 18, 2023 7:57 AM

Well, this was quite a mess. I tried all the good fixes mentioned, but no love. I tried logging out of all Apple services and syncing, I tried making another iTunes library, no change. However, I did notice something along the way. My Music Library had moved. It was not where it used to be. I finally decided to go nuclear. I installed MacOS over the top of what was already there using Recovery mode. Upon attaching the USB cord, the Mac immediately said I needed to download new software for iPhone 14 to work with this Mac. It did so and installed it. No love. Still hanging on "determining items to sync." Then I went for the iPhone erase, did an iPhone Restore from the Mac (firmware and all) and set up as a new phone, manually, without bringing over any apps or data. Not restore from a backup. Of course my music library was empty, so I imported a CD and synced. Worked! Then I linked to my real music library (which moved) and synced. Worked!


In the end, I think the real problem was my trial subscription to Apple Music, which I cancelled. It moved my music library from a shared folder to my home folder and rearranged the files in the library. Sync troubles seemed to start at about that time.


I have yet to determine how much pain and agony will come from not moving my apps and data over from a backup. I'm afraid the problem will come back if I restore from a backup.


Thank you for all the tips!

3 replies
Question marked as Top-ranking reply

Mar 18, 2023 7:57 AM in response to TheLittles

Well, this was quite a mess. I tried all the good fixes mentioned, but no love. I tried logging out of all Apple services and syncing, I tried making another iTunes library, no change. However, I did notice something along the way. My Music Library had moved. It was not where it used to be. I finally decided to go nuclear. I installed MacOS over the top of what was already there using Recovery mode. Upon attaching the USB cord, the Mac immediately said I needed to download new software for iPhone 14 to work with this Mac. It did so and installed it. No love. Still hanging on "determining items to sync." Then I went for the iPhone erase, did an iPhone Restore from the Mac (firmware and all) and set up as a new phone, manually, without bringing over any apps or data. Not restore from a backup. Of course my music library was empty, so I imported a CD and synced. Worked! Then I linked to my real music library (which moved) and synced. Worked!


In the end, I think the real problem was my trial subscription to Apple Music, which I cancelled. It moved my music library from a shared folder to my home folder and rearranged the files in the library. Sync troubles seemed to start at about that time.


I have yet to determine how much pain and agony will come from not moving my apps and data over from a backup. I'm afraid the problem will come back if I restore from a backup.


Thank you for all the tips!

Mar 15, 2023 7:40 PM in response to ILuvMnMs

ILuvMnMs Said:

"iPhone 14 won’t sync with late 2015 iMac.: I upgraded from iPhone XR to iPhone 14. Sync always stops at 'determining items to sync.' Just keeps churning. Won’t sync on other accounts either. My wife’s iphone SE will sync on all accounts. Photos won’t load for importing either."

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Troubleshooting iPhone Sync::

(Applies to Intel-based Macs Only): Sometimes when changes are made to the system(i.e. updates), system configurations (i.e. for Sound) become manipulated, technically. So, reset the SMC and NVRAM.


  • Boot into Safe Mode:

When you boot into Safe Mode, items load by default, with certain settings and caches set aside. So, hold down the shift key upon boot. See what happens then.


  • Create A New Admin User:

For temporary and troubleshooting purposes, create a new user, and then try this once more. Trash the user, once done troubleshooting.

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iPhone 14 won’t sync with late 2015 iMac.

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