lost files

How you recover the music will depend upon several factors.

First of all, ten years ago, when you added music to "iTunes", you were simply adding it to your Library, not an online storage facility:

• so the first question is - are you looking in the same Library (on the same computer) that you added the music to ten years ago?
• is that the last time you saw your music?
• did you back up your music?
• where did the music come from in the first place, did you import it from CDs, or buy it from the iTunes or other online stores?

I assume, from what you say, that you no longer have the old computer (I didn't think to ask about that). Usually, one copies the complete music folder (with associated iTunes control files) onto the new computer.

Although you have the iPod, with music on it, synchronisation is one-way, from iTunes to the iPod. (The exception is purchases from the iTunes Store.) There are methods for retrieving music from an iPod, back to iTunes, and you can read about some of those at Recover your iTunes library from your iPo… - Apple Community . If anything there helps you, make sure you let the author there know (that's user tt2).

The only alternative is to re-build your Library, from scratch. To do that, put copies of each song into the Music/iTunes/iTunes Music folder on your current computer (sometimes, you may find the last sub-folder is named iTunes Media). Then use the iTunes command to add files (and folders) to the Library.

• If you can recover any music from your iPod using the tip page mentioned above, start with that
• Music purchased from the iTunes Store should be available for you to download, once you sign into your iTunes account in your iTunes Library
• Music purchased from other online stores should also be available for re-downloading, from your account with that store
• Next, copy any music not already recovered, from the flash drive. Artwork should already be part of each music file, so there should be now need to copy that. The exception is .wav files, which cannot store artwork in the file
• Copy from CDs into your new iTunes Library

Once you have added files to your computer, the only ones that will show up in your Library immediately will be the purchases from the iTunes Store. For everything else, you will need to "add files (or folders) to your Library". The commands are:

• for a single song - File/Add File to Library and in the dialogue that pens up, navigate to the folder and choose the file
• for a folder, containing either just one album or several - File/Add Folder to Library, navigate to and then select the folder you wish to add

I recommend that as you re-build your Library, you maintain a backup as well. Even computers and their drives fail.

I use a programme called Sync Toy to back up from the Music folder to an external drive (and no, I receive no reward or compensation for suggesting it).