20.07.2009.
How to JB 2ndGEN iPodTouch?
This tutorial is meant to help those having trouble breaking their 2nd generation iPod Touches. This guide is made for Windows, but the directions are similar on a Mac.
First, you must upgrade your device to software 3.0 though iTunes. Pay the $10 free to upgrade ( or find another way to get the firmware 
) and continue. If you update through iTunes then the process is expained in iTunes. If you obtain the Firmware from another source, save it in a location that you won’t forget. Go to your iPod in iTunes, hold “shift” and click “restore”. It will open a file browser window and you can upload your saved firmware. Let the iPod update. Note that your files on your iPod will be replaced. Your iTunes files will resync when the update is complete.
Next, download the latest version of Redsn0w from HERE and install it to your computer. Run Redsn0w. You will be prompted for the firmware file. If you bought it through iTunes, it will be saved where iTunes keeps its restore files. If you need to, you can open iTunes and do the “shift-click” method again. Use the path given. If you obtain it from another source, it will be where you saved it. Follow the directions in the Redsn0w program and it should be jailbroken. Have fun!
If you had the tethered 2.2.1 jailbreak, restore it to your original firmware in iTunes first. Then proceed with the steps.
Troubleshooting: If something goes wrong, RESTART YOUR COMPUTER, then retry. That is the main cause of errors. Ask me questions here after you have already tried restarting.
