I have an older 80GB ipod classic. I recently purchased an album, but can't get it to transfer from the remote harddive I store all my music on, over to the ipod. Used to sync automatically. Anyon help?

If your music is stored locally and not in the cloud, and hasn't come from an Apple Music subscription, then it ought to transfer if it is part of the content that is selected to sync. Connect the device to iTunes and select the icon that appears on the top row.

Then check the sync selections on the various pages before trying to sync once more.

tt2

See Recover media from an iPod.

FWIW the iPod doesn't get authorized, the computer does. A device can hold protected content from up to five different Apple IDs. Yours must have purchased content from more than one. Transferring all purchases potentially leaves non-purchased content to recover. See the user tip and reclaim everything.

tt2

For what its worth.

iTunes will only transfer protected content to a device if the computer is authorized for the account in question.

iTunes will only transfer protected or purchased content from a device if the computer is authorized for the account.

It seems I missed the fact that you're having trouble copying to the device, not from it. Try If iTunes prompts you to authorize your computer when you try to play iTunes Store purchases - Apple Support.

Then again if you're getting the erase and sync warning perhaps you do want to recover the media. Is all your content in your library? If you've had to rebuild it at some point then it may now have a different internal ID than it had when it originally added the media.

In the AppleSpeak surrounding such terms as authorization and association the classic is classed as a device, but not an iOS device.

tt2

So visit the user tip that I've suggested: Recover media from an iPod.

Recover all of the content that is on the device into your library.

Add any other iTunes compatible media that is on your computer into your library.

See DeDuper for a script to clean out duplicates.

See Make a split library portable to organize it properly on the external/remote drive.

iTunes is more reliable with locally connected external drives. Remote drives are more suited to backup.

See Backup your iTunes for Windows library with SyncToy to back it up.

Once all of your media is stored tidily in one place you can afford to erase and sync the device with a selection of content from it.

N.b. iTunes 12.7 cannot add iPod clickwheel games to a classic, and might not recover those that are on it either. If you need to extract any that aren't in your library, or add any that you have to the device, then you may need to install iTunes 12.6.3.

tt2

I'm having the same problem, but I am unable to authorize my 160 GB Ipod Classic. It continues to say "this computer is already authorized" but is not authorizing the Ipod. I cannot sync because I'll loose music that is no longer on my computer, since syncing removes all music from the ipod before transferring.

I continue to get a warning that says "Some of the items in the Itunes Library, including "X" were not copied to the Ipod "My Ipod" because you are not authorized for them on this computer." I am logged into my account, have authorized my desktop, but can't figure out how to authorize the Ipod.

fwiw? I have only 1 Itunes account, and only use a computer. Also the Ipod is technically a computer, it has been "authorized" as a computer before.

not all of my content is in my library, or on my computer, so syncing or restoring is not an option. and I've tried all of those options from apple support, none have worked.

I have the ipod in disk mode and connected to the computer but it is not showing the hidden files.

Are you running on Windows or Mac?

tt2

Windows

See Show hidden files in Windows.

tt2