iDevice syncing weirdness

It’s been bugging me for quite a while so I thought I’d see if anyone here has a clue about what’s going on…

I have a Music library of many 1000’s of tracks, mostly ripped, but some purchased. I have an iPhone 13 Mini, an iPad Pro 12.9, and an older iPad Pro 10.5, all with up to date OS’s. I have iCloud syncing turned on.

I back up the iDevices to my 2015 iMac running 11.6.2, and to iCloud before doing any OS updating. Every time I plug an iDevice into the iMac the Finder does its automatic sync routine and two weirdnesses occur:

  1. the Finder on the iMac says it can’t find a few tracks that are in my Music library to sync and I have to click OK to continue (I can click a dropdown > to see more details but it doesn’t help me understand what’s going on.) And,

  2. the Finder then proceeds to copy the same 190 tracks from Music on the iMac to the iDevice. As far as I can tell those 190 tracks are already available to play on the iDevices, so why is Finder copying them every time I plug in to the iMac?

Thanks for any ideas.

Jack Clay

Indeed, iDevice syncing be very weird/sketchy. In re:

  1. Once you click “OK” do all the rest of the tracks sync and can you see which ones do not?

  2. Can one exclude Music? You seem to mostly use “your own” music and does the overwhelming majority of that sync as desired?

I am a streaming fool because I detest these complexities and I also love so many different kinds and eras of music that if some of “my” music isn’t “there” I’ve become zen with it.

Let us know how this shakes out.



I had a similar situation several years ago. My solution was to delete all music tracks from the iDevice then re-sync from scratch. The problem went away.

All my music was ripped from CDs…none purchased…none downloaded…so all tracks were available from my Mac.