Last version of iTunes that will sync an iPod Classic?

To my surprise, I connected my vintage iPod to the latest version of iTunes and it actually worked. First, it said that it needed to download some compatibility software. Then it synced all of my new music. I have a 2nd old iPod. I connected that one and bingo! It worked too. This was on Feb 10th 2024. I am very happy! It hadn’t worked in 3 years.

Again, all versions of iTunes should be able to sync to an iPod classic. Very occasionally there might be an issue with some function in the last release, in which case switching to the one before usually resolves things. iTunes libraries are forward compatible. If you need to revert to a slightly older build of iTunes, and it won't open your library, you should be able to copy a recent backup out of the Previous iTunes Libraries folder that is compatible with that build. Obviously the longer you use a new version of iTunes the more changes you will make, and the less desirable rolling back will be.

See the very bottom of Troubleshooting issues with iTunes for Windows updates - Apple Community for recent installers and Empty/corrupt iTunes library after upgrade/crash - Apple Community for details of how to roll back your library if required.

tt2

What version of Windows are you running, and is it 32- or 64-bit?

To underscore the fiend's point that your copy of iTunes is outdated note that apart from iTunes 12.6.4.3 all other builds with a lower version number than 12.7.2.58 have outdated encryption support and are no longer able to connect to the iTunes Store for account management purposes. See About App Store and iTunes Store availability - Apple Support for more information.

tt2

All versions of iTunes will sync with an iPod Classic.

I'm not sure why you would need to be connected to the internet or the iTunes Store in order to work with your iPod since the Classic cannot use any of the features you mentioned. I suggest that you cancel all attempts to access the store (more of that in the next paragraph) and work just with your library and the iPod.

The reason that your iTunes is having issue connecting to the store is because it now requires iTunes 12.7.2.58 (I believe) as a minimum in order to use the store. You will not be able to authenticate with the iTunes Store with the version of iTunes that you are using. That does lead to the question of why you're using such an outdated version of iTunes?

• • On Windows 10 (or 11), the current version of iTunes (on the day of writing) is 12.12.9.4
  • If you have Windows 7 (or Windows 8) the most recent version of iTunes for that is 12.10.11.2. No later version of iTunes can be installed on these operating systems

Even if you can resolve the authentication issue and use your iPod with 12.4.3.1, that is such an old version that I would recommend that you update to the most recent version that your computer can use (see above). The version you're using is seven years old. There have been countless updates to iTunes since then, to address security issues and resolve bugs.

dflint wrote:

The reason I didn't want to upgrade my itunes to the latest version, is I've read you loose syncing ability with older ipods.

But that is not true. As stated, all older models of iPod will work with the current version of iTunes. (tt2 will correct me if I'm wrong!)

Apple has discontinued support for all ipods from what I've read, and I previously had a newer version that would not mount my old ipods in itunes.

Well, even that isn't actually true. Apple no longer offer a repair service for iPods; many (but not all models) no longer receive software updates, but iTunes supports all iPods and your fellow users here (on a site provided by Apple) are able to help with many, many issues, including iPods that are not recognised by iTunes. Yes, it does happen - but it is fixable. See:

• • this Apple support document: If your computer doesn’t recognise your iPhone or iPad – Apple Support (UK)
  • this article, written by turingtest2, who has responded to you in this thread: iOS device not showing in iTunes for Wind… - Apple Community

To expand on this point, Apple do provide updates, when necessary, for discontinued models of iPod:

• the 7th generation iPod Touch, which was discontinued in May 2022, continues to receive bug fix updates
• the 6th generation iPod Touch, which was discontinued in May 2019, received its last update in January 2023 (a security fix, I believe)

Consider this: updates offer:

1. 1. a new feature
   2. enhancements to existing features
   3. fix stability issues
   4. a security update

• If an iPod has been discontinued for some time, it's unrealistic to expect Apple to offer new or even enhanced features for it. So old iPods will not be updated to provide points 1 or 2
• once an iPod's software is stable (to an acceptable standard) then it requires no further updates. Hence , models such as the iPod Classic, the nano, etc. no longer require updates (that's point 3)
• the iPod Touch, which has the ability to interact with the internet, opens up the possibility of security issues. The two most recent models of Touch have received security updates, in order to address this. The 5th gen Touch was discontinued nine years ago, so it's hardly surprising that it and even older versions are no longer being updated. So to ensure that security is not compromised, those older models, as well as older versions of iTunes, cannot access the store

Some of the older songs I have bought on itunes now require authentication to sync or play (which is what is now broken)... it annoys me that I have to log in to utilize something I bought already. Guess I'll have to convert it when I am able to play it again.

As also stated, iTunes 12.7.2.58 is required in order to use the iTunes Store, which in your case, means authenticating songs purchased from the store. Again, for security reasons. It's not "broken"; you haven't installed a version of iTunes that ensures that the iTunes Store is not compromised.

Try again. As of Feb 11, 2024, it is now compatible with iTunes again…