Will my Classic 80GB Ipod sync with latest Itunes on windows 8.1?

It should still with both the iMac and laptop with Windows 8.1, running the latest iTunes. Even my ancient iPod from 2003 works fine with the latest iTunes on my Mac.

If you have that "iMac 21.5 desktop" now, what happens when you try to connect it? Maybe Apple never mentioned that, because it's not true. 🙂

That's the 6th gen iPod, which is an earlier version of the currently sold "iPod classic." Did you try connecting it to your iMac?

When you do, what happens on the iPod's screen?

In iTunes, make sure the sidebar (along left side of window) is visible. If it's hidden, from the menu bar, under View, select Show Sidebar. When connected, the iPod should be listed under DEVICES. It does not appear there?

When you plug in the iPod to USB on the iMac, what does the screen on the iPod say? Do not disconnect? Just shows the screen menus? Shows the charging symbol?

You said it does not sync, but does that mean it does not appear in iTunes (in the sidebar under DEVICES)? Or does it appear listed in iTunes, but you cannot get it to sync?

If it appear in iTunes, but does not sync, it may be because it is currently set up to sync with your Windows PC's iTunes library. For an iPod, automatic syncing only works with one iTunes library at a time. And iTunes syncing is generally in one direction only, from iTunes library to iPod.

I'm actually saying it is possible to sync your iPod from your iMac. I have not seen anyone report here that newer iMacs cannot sync to older iPods. If you want use automatic syncing, you will have to pick the computer you want to keep "in sync" with your iPod.

However, that does not mean both computer cannot have the same songs in their iTunes libraries. If one of them is considered your "master" library with ALL of your content, you can put that complete library on the other computer. This document explains how to transfer your iTunes library from one computer to another.

http://support.apple.com/kb/ht4527

See the method called External drive.

Another way (if you don't mind spending $25), is to use Apple's iTunes Match service. This puts a copy of your iTunes music library in iCloud, and makes it accessible from other computer and Apple iOS devices (such as iPod touch, iPad, and iPhone). From the iCloud copy, you play songs by streaming and also download any song (or all the songs) to another computer. I use iTunes Match, but keep a full copy of my iTunes music library on my primary Mac's drive. I can play my songs on other computers and devices that I own, from the copy in iCloud. NOTE: iPod's (except iPod touch) cannot sync with iCloud directly, so you'll need to have one computer running iTunes (with a local copy of your iTunes music library) for syncing with the iPod.

The subscription fee is annual, but downloaded song files remain playable even if you stop subscribing to iTunes Match. You just can't access the iCloud copy of your iTunes music library anymore, if you stop the subscription. (It also pays for ad-free use of the iTunes Radio service.)

I am trying to keep all my new purchases available on both computers and the Ipod.

You can download previous purchases from the iTunes Store at no cost, from another computer. Sign in to the iTunes Store using the Apple ID used for making the purchases. On the iTunes Store Home screen, click Purchased under QUICK LINKS. On the Purchased screen, you can find and download previous purchases. So even without iTunes Match or transferring your complete iTunes library, you can easily keep recent purchases "in sync" on both computer, and sync the iPod to one of those computers.

how do I properly clean off the iPod?

If the iPod is currently set up to automatically sync with one iTunes library, and you set up automatic syncing with a different iTunes library (on the other computer), that will replace the existing content of the iPod. So, there is no need to "clean it off." However, you can do a Restore, if you want to give the iPod a fresh start. In your case, if the iPod was previously used with a Windows PC, and you want to start using it with a Mac, a Restore reformats the iPod's storage for Mac use. It's not required, because Macs can use the Windows format. If you go back the other direction, it is required becaues Windows PCs cannot use the Mac format.

The Restore button is on the iPod's Summary screen in iTunes. It will erase the iPod, reinstall its software, and set it to default settings. It's what some people call the "factory" reset. You can then set it up to sync as desired.

Can anyone help?

I have been reading your post and answers and trying to make sense of this.

I plug in my ipod classic into my imac running maverick (which i just downloaded) and

Ipod says "Connected, eject before disconnecting" but Itunes (11.1.5) does not recognize the Ipod at all, not at the sidebar and not anywhere. My imac recognizes it as a drive. It shows it on the top right corner, right next to my external hard drive.

What should I do. Please help.

Disconnect the iPod (eject it first by dragging its desktop icon to the Trash). Restart the iMac. Do this to Reset the iPod, in case it is stuck in Disk Mode or something

http://support.apple.com/kb/ht1320

After the Reset, does the iPod shows its normal "home" screen, where you can select to play songs, etc.?

If the iPod operates normally when disconnected, after the iMac completes startup, run iTunes, then connect the iPod. If the sidebar (along left side of iTunes window) is showing, it should appear there listed under DEVICES. If the sidebar is not showing, there should be a device button near the upper right corner that says "iPod."

Tried what you told me.

Itunes (not imac) still won't recognize the ipod. since I upgraded itunes this has happened.

When ipod is not connected to the itunes it works great, (although I lost all my music on it and can't really listen to anything but it works, it toggles. All buttons seem fine)

When ipod is connected it just says "connected, eject before disconnecting" and itunes does not recognize it in the sidebar nor on the top right.

Any other suggesstions?

It may be a problem with your iTunes installation, since the system seems to see the iPod. If you have not already, I would download the latest version of iTunes and install it again

https://www.apple.com/itunes/

apple ipod classic 80GB