What's the safest, cleanest way to jailbreak my ipad1?
I'm running iOS 5 I believe.
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I'd recommend redsn0w. It's what I used. It's not hard to do, plus it has a lot of other tools in it that can help if you mess up. The link to the official download and a quick tutorial can be found here. You'll need to upgrade to iOS 5.0.1 beforehand.