My iPod Classic won't sync to my new MacBook Pro

I just purchased an early 2015 MacBook Pro 13 inch. It runs on OSX El Capitan, version 10.11.4.


I'm running iTunes version 12.3.3.17 on it, and the Apple Store did a migration for me and transferred all my previous iTunes libraries over perfectly.


I use a 160GB (Fall 2009) iPod Classic running on the up-to-date software (2.0.4), which has previously displayed zero problems. The iPod is recognised by my iTunes but won't sync when I click on Sync. There are no error messages, it briefly flashes as if to begin the syncing process and then doesn't follow through.


I have yet to restore the iPod to factory settings.


Does anyone have similar experience? How do I get my iPod to sync on this new MacBook?

iPod classic

Posted on Apr 27, 2016 6:45 AM

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3 replies

Apr 27, 2016 9:20 AM in response to ebarlow86

The iPod may not be set to Sync Music (automatically) with the iTunes library on the new MacBook. Therefore, clicking the Sync button does sync, but nothing is set up to sync. To check, select the iPod in iTunes (click its device button on horizontal bar) to show the iPod's settings screen in iTunes window. Along the left side (in the sidebar), under Settings, click Music. The iPod's Music settings screen is shown to the right.


NOTE: Any songs (and playlists) on the iPod that are not in your iTunes library will be lost.


Checkmark the box for Sync Music, if it's not already. This turns ON automatic syncing for music between the iPod and this iTunes library. Below that, if your iTunes music library can fit on your iPod, you can choose the option to sync Entire music library. Then click Apply. iTunes syncs your songs and playlists in this iTunes library to replace the iPod's existing content. Therefore, make sure your the iTunes library on the new MacBook has ALL of your songs and playlists.


Going forward, iTunes keeps the iPod "in sync" with changes to your iTunes library, when you connect it (or click Sync if already connected).

Apr 27, 2016 12:21 PM in response to ebarlow86

If the iPod has data corruption... Try putting the iPod into Disk Mode


Putting iPod into Disk Mode - Apple Support


Run iTunes and connect the iPod. If iTunes pick it up, it may prompt you to do a Restore. The Restore erases the iPod, reinstalls its software, and sets it to default settings. If there is no hardware problem, the data corruption problem should be resolved after the Restore, and you can re-sync your iTunes library to the iPod; you can follow the same steps (in my previous reply) to set up automatic syncing.

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My iPod Classic won't sync to my new MacBook Pro

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