I'm not an iOS guy at all. An acquaintance was asking me. No jailbreak methods or hacks to make this happen?
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I realize this is an old thread... but... there are a few jailbreaking options I've tried. I got this device a week ago, and it came with iOS 4.2.1. I first tried this on it:
Greenpois0n.com
That seemed to work for a bit, but I couldn't find enough usable apps on it for my tastes. After more research... I got this instead:
Whited00r Upgrade Unlock Jailbreak iPhone 2G/3G iPod Touch 1G/2G
It's essentially a hacked version of iOS 3.1.3, with some features of iOS 5/6 added onto it. It comes with two app repositories, Cydia, and App Time Machine. ATM has older versions of apps that cracked, but safe to use with whited00r. I still have iTunes installed on my Windows 8 PC, but most of the maintenance I perform with this iPod is with the iTools app from iTools.hk.