My friend has a 2nd generation iPod touch running 2.2.1, and he wanted me to jailbreak it. I thought I knew how to do it, but then I realized that blackra1n only works for OS 3.0 and greater. And according to the Dev-team's website, so too is redsn0w. So, right now what I want to know is, what are my options for a jailbreak if: They stay on 2.2.1 (Will this mean they have to re-sync and reinstall everything back onto their iPod?) They upgrade to 3.1.3 (Will they have to pay? Will it be untethered? Will this mean they have to re-sync and reinstall everything back onto their iPod?) They are running the latest version of iTunes (9.1.2).