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I'd highly recommend against tampering in any fashion, including sending e-mail to himself, with the individual's system. The last thing you want is for the guy to flip out and call the FBI and get you busted for illegally accessing his system.
Just because it's insecure doesn't mean it's ok to look around, which is something that I'm sure a lot of us (myself included at times) have trouble remembering.
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Eat antimatter, Posleen-boy!
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