iPod Classic 160g does not sync

See this post on reinstalling either the current version of iTunes or a recent one that works better for you: Re: Re: iTune Crashes on latest release.

You do not want to sync if there is content on the device that isn't in your library. See this guide on recovering your media from your device: Recover media from an iPod. As long as it shows in Finder when in disk mode you can get the content off it now before worrying about iTunes.

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Connect the device to iTunes and select the icon that appears on the top row.

Then check the sync selections on the various pages such as music, movies, etc. before trying to sync once more. Perhaps it is only syncing one rarely updated playlist. Make sure the content in your library is checked and downloaded. iTunes cannot put Apple Music items or anything that is in the cloud onto an iPod classic. If needs be restore the device and reload it.

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I have this same issue and have opened a ticket with Apple support. Tested three (3) different iPod 160GB, several cables, direct USB connect, Hub connect, powered-hub connect and a Elgato Thunderbolt 2 dock ports.

The iPods all appear in System Information under USB but iTunes seems to be disconnecting them. Everything under current release at the time of this post.

iTunes disconnects.

On the iPod Classic 160GB models, and I've tested four (4) iPod Classic 160GB with several different 30-pin cables, the iPod Classic will get to the point where the "Sync" animation appears on the iPod display and then it immediately disconnects. The behavior looks like iTunes or iTunesHelper is doing the disconnect. If iTunes doesn't launch, the device appears in Finder, as expected. (It actually appears in Finder very briefly, even if iTunes does the disconnect.)

Each IpoD appears in the System Information screens under USB in the appropriate USB controller, whether that's the Mac Pro USB port, a USB Hub or a dock like Elgato. Under each of the wiring patterns, the behavior is the same.

I then tested the previous generation iPod Classic, two (2) 60GB iPod Classic units. They seem to behave differently, appearing in Finder but never being seen by iTunes and never being disconnected.

It seems like the USB2 article Apple published on June 6th might be relevant to this situation.

Thanks for your comment and suggestion.

Apple Customer Service called me today, 26-June-2017, to inform me the Apple "Engineering Team" has declared the iPod Classic 160GB to be "obsolete" and the functionality to sync with iTunes will not be restored. The resolution is to purchase a new and smaller iPod Touch device (which also has an uncertain future).

I am now evaluating third-party software to replace iTunes, a product called Swinsian, the seems very promising for iPod Classic devotees. This involves making your iPod Classic work in Disk Enabled mode. Three of my units were already set that way, but a fourth unit seems to accept the setting on my older MacMini but not seem to have it when I connect to the mac Pro under Sierra. You also want to turn off "Automatically launch iTunes" upon connection.

It's very disappointing that a new MacOS machine would not work with the iPod Classic. Sometimes "used" is better than "new".

Not sure if related, if your iPod was originally synched on another computer, say an ex GF or wife, or another mac you used to own, the classic will not work. I bought and downloaded cd's on another iMac with my iPod classic, but had to get a new one. All the other music I bought is now wasted, I cannot get it on the new IMAC. So if I purchase or download cds to the new MAC, it will not synch ON MY CLASSIC. APPLE HAS SCREWED US OVER ON THIS ONE!!!

Cannot Sync my 160GB iPod classic with ITUNES 12 either. The problem is this is my music player on my boat and would require replacing the head unit on my boat and will cost a good deal more than just buying a new iPod alone. Has anybody found a way around this end of support issue?

Apple may not be actively supporting the iPod classic any more, but you should still be able to sync content to it using iTunes. Have you tried another cable or checked for fluff in the docking port? Different contacts are used for charging so you might not notice an issue that only affected data.

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The latest patch to iTunes seemed to have corrected the issue for both my 60GB iPods and my 160GB iPods, so even if officially unsupported, they are working again. I might continue to play with Swinsian, too, though. Just in case.

I can confirm for me as well that my 9+ year old iPod Classic 160 was able to sync successfully again after the latest iTunes patch. It was struggling mightily to connect but as soon as the patch was applied it worked. Hopefully it will remain stable for a while longer.

The iTunes is sort of installed, but it won't save CD albums properly.

And I can't back up the 6000 plus songs ether, as it won't sync.

We did all the updates we could.

We scheduled an appointment at local Apple store tomorrow, they sent an email telling me to back up!

How to?

See Recover media from an iPod.

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Is it set up to sync automatically? Select iPod in iTunes (click its device button on horizontal bar) to show its settings screen on iTunes window. Along left side (in the sidebar), under Settings, click Music. To the right, the iPod's Music settings screen is shown. Is the checkbox for Sync Music checked? If it's not checked, your iPod is not set to sync music automatically.

NOTE: When you change that setting, any songs on the iPod that are not in your iTunes library will be lost.

If the checkbox for Sync Music is not checked, checkmark it. Below that, if your iTunes music library fits on your iPod, choose the option to sync Entire music library. Then click Apply. iTunes may remove all of your songs from iPod, and then sync your entire music library back. If your iPod has a problem with its hard drive, this may cause an iPod that functioned "as is" to no longer function. If it works, your entire music library will be on the iPod and iTunes will keep it up to date with changes, when you connect it (or click Sync if already connected).

I'm having the same problem except I'm on windows 7 (and hesitant to upgrade to 10). I'm running up to date itunes and ipod software (itunes 12) for my ipod classic 160gb which is only a couple years old. I've troubleshooted restarting computer, itunes, ipod, different cords, usb ports. Windows recognizes my ipod as an ipod. However itunes doesn't. The iPod itself works fine. I've been having issues for a couple of months. Everyonce and a while it will sync, but I can't find the reason for it. I've also tried turning automatic sync on and off in the preferences.

I'm wondering if it's worth the effort to go back to itunes 11? I'm really unimpressed with Apple at this point.