Lost content on iTunes

Syncing between iTunes and iPods has always been one-way, you cannot simply copy music back from an iPod to iTunes. There are programmes for recovering music from an iPod and putting it back into iTunes, although I've never tried them and I believe they all cost money (after a free trail period). Check this tip, from user tt2, that has more information about recovery software: https://discussions.apple.com/docs/DOC-3991

I have also read that Window Media Player can rename or move files, which will cause issues with iTunes, although I have never seen any evidence of this myself.

So - if your missing songs are no longer on your hard drive (not even in the recycle bin) and you have no back up, your only options are to obtain them again from your original source (possibly at additional cost to you) or try the software mentioned in tt2's article.

Other methods to replace your lost music:

• • music from CDs, that you no longer have - buy the albums again
  • music purchased as digital files - most (but not all) stores will allow you to download previous purchases again. You do of course, need to sign into your account with that store
  • music downloaded from artist websites etc. - go back to that site and re-download if possible

Although you won't thank me for pointing this out now, you will do in the future: back up your Library!

• Music on portable devices such as iPods and iPhones is not a backup
• Portable devices get lost, stolen or dropped
• As you have already discovered, Apple devices are not able to copy back from the device into iTunes
• The hard drive on your computer can fail
• I read recently of someone who believed they had a backup of their Library, only to realise that they had their "backup" on the same hard drive on their computer

So make a backup of your existing Library, before that too gets lost. Buy yourself an external hard drive and copy your music to that drive. You can use a bit of software called SyncToy to copy from one drive to the other (just search for SyncToy online).

iTunes does not have the ability to randomly delete music from your Library, so perhaps it has just lost the link to the file.

First of all, what is your definition of "deleted"?

1. 1. if you mean that the song is still listed in your iTunes library but you get a message telling you that the song cannot be found (and/or there's an exclamation mark to the left of the song title in the Songs view), the most likely cause is that someone, or another programme, has deleted, moved or renamed the file (or the path to it), which means that iTunes no longer knows where to find the file for that song
   2. if you mean that there song is no longer listed in your iTunes Library, I suggest that you search for the song's file in Windows File Manager, to see if the file still exists. A song usually has a filename that closely matches the title of the song. For example, if I want to find a song titled Deep Forest, I search for deep forest:

As you can see from the screenshot above, not only did the search find the song titled Deep Forest, but it also found the album from which it came, plus a few other associated items. My screenshot shows a Windows 7 search, but Windows 10 is almost the same. If the search does not show the file location (that you can see in the right column of the screenshot), right-click the item and choose Open file location form the pop up menu.

If you let us know which of the two options above applies, we can then try to see whether we can find them and get them back into your Library again.

For an iPod classic it is usually possible to extract the media without resorting to third party tools. See Recover media from an iPod - Apple Community for a more focused user tip.

tt2