Computer programs abound for solving this problem, though most of them are either pay apps or needlessly complicated. Luckily, there is one simple way to get all your music off almost any iPod or iPhone, no jailbreaking required. Here's how to do it.
Note: This works with every iPod except old click wheel iPods that were formatted for use with a Mac. So, if you're a Mac user and you have a click wheel iPod (as opposed to an iPhone or iPod touch), you'll still have to use one of the other, more complicated methods.
Step One: Find Your Device's Music Folder
If you're on an older iPod, plug it in and start up iTunes. Click on the iPod in the left sidebar and check the box that says "Enable Disk Mode". Then, open up Windows Explorer and click on the iPod in the sidebar. If you don't see the iPod_Control folder, go to organise > Folder and Search Options and hit the View tab. Click the "Show Hidden Files, Folders, and Drives" radio button and hit OK. You should see a folder called iPod_Control show up, in which you'll find all your music.
Step Two: Open Up iTunes
Step Three: Drag, Drop and Wait
It isn't the perfect method, but it's the easiest, most consistent method we've found, and it's completely free. If this doesn't give you everything you want, try out one of the programs we mentioned in our guide to copying music from your iPod, just know that you may have to pay for most of them. Good luck!
P.S. Got your own favourite method for getting music off an iPod or iPhone? Share it with us in the comments.