One of the failings of iTunes is the inability to copy music files from the iPod to your iTunes library without third party utilities. I suspect Apple did this by design to keep we iTunes customers from copying our DRMed music. I recently rebuilt my Tablet PC and wanted to copy my 18 GB of music residing on my iPod over to the Tablet so my library would be filled again. A gotcha lurks when you install iTunes and your iPod onto a new computer because iTunes is set by default to replace your iPod library with the desktop library the first time they are partnered. Of course since your iTunes library is empty it promptly wipes out your precious music on the iPod leaving you with no library anywhere. Ouch. There is a simple way to prevent this and also copy your iPod library to the desktop without any third party software.
iTunes won’t let you configure the iPod to prevent the auto-syncing until AFTER the iPod is connected to iTunes. It is imperative you do not partner the two libraries when asked by iTunes, tell it no so the auto-sync doesn’t wipe your iPod clean leaving you a blubbering idiot in the process. Once the iPod is connected and set to operate as a hard disk on your PC exit iTunes. Go to the iTunes directory on the Windows machine (My Music/ iTunes by default) and delete the XML file and the ITL file which is the library database installed when you hooked up the iPod.
With those files deleted the iTunes library is now empty as it should be for this process. Navigate over to the iPod in My Computer and make sure you set the folder options to show hidden files. Find the hidden folder called iPod Control and even though it’s filled with many files with nonsensical names this is in fact the music library on the iPod. Copy that folder to anywhere on the PC which will take a while if you have a lot of songs. When this copy is complete open iTunes and in the Files menu tell iTunes to Add a Folder and select the iPod Control folder you just copied over. You could actually do this straight from the iPod without copying them all over but I was nervous something might happen to the library on the iPod so I copied them first.
Before you do the Add a Folder mentioned above make sure iTunes is set to manage your library and to copy files when adding to iTunes. This is important to get iTunes to organize the songs using the ID3 tags in the song files you just copied over. That’s it– you have all your iPod songs now properly copied to the desktop and nicely organized and in the iTunes database. Note that when you first connect the iPod to the computer after you set iTunes to auto-sync it will wipe the iPod clean and sync the new iTunes library back to the iPod. It seems like a silly step but since the two libraries are the same anyway it doesn’t hurt anything, it just takes time. It is necessary to make sure the databases are identical. Once it’s done you can delete the iPod Control folder you copied on the desktop since iTunes has copied the songs into it’s own directory tree.