If you've been looking high and low on the iTunes interface for the button that allows you to transfer songs from your iPod back to your PC, you've been wasting time. For various reasons, chiefly among them piracy concerns from record labels who contribute content, there is no such function built into iTunes. But that doesn't mean it's an impossible task; with one exception, it has simply fallen to third-party developers to create software that will allow you to make the transfer. Here's how you do it.

Purchased Content

There is one exception to the block on transferring songs from your iPod to your PC -- purchased music. With iTunes versions 7 and higher there is a method by which you can transfer all purchased content (either bought on the PC or your iPod) back to the PC. The downside to this is you can't choose specific tracks. It's an all or none proposition. Here are the steps to accomplish this: 1. Make sure the computer has been authorized for the account by choosing "Authorize Computer" from the "Store" menu in iTunes. 2. Enter your iTunes user name and password. 3. Once the computer has been authorized, select the "Transfer Purchases" option from the "File" menu in iTunes. Your purchased content should all transfer back to the PC. Make sure you don't select the "Erase and Sync" option.

Third-Party Software

A variety of third-party software applications have arrived to fill the iPod-back-to-PC void. Companies such as YamiPod and SharePod provide free software. Others have a one- or two-week trial period and some charge in the $20 to $40 range. Some are little more than bare bones utilities that copy only the music files. Others are more robust programs that transfer playlists, ratings and play counts too. No matter which software you ultimately choose, make sure you have the latest version compatible with the latest version of iTunes.

Jailbreak

Some people have learned to perform what is called a jailbreak and actually go into the iTunes programming code and change it to allow the transfer from iPod back onto your PC through the iTunes software itself. Apple's stance on this is that jailbreaking is illegal, but they haven't seen fit to press the charge in court. The term jailbreak is the process of unlocking the software to allow music transfer in both directions. As with almost any topic, the Internet provides plenty of information about this technique, but make no mistake, this is not condoned by the manufacturer of iTunes and iPod.

Source:

iLounge: Copying Content from Your iPod to Computer

LifeHacker: Copy Music from iPod to Computer