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Rooting sites
www.smashthestack has some kewl r00ting challenges
Ever heard of pulltheplug ? Most people here wouldn't be able to complete a single challenge on that site (That include HBH Guru people).
http://pulltheplug.org/wargames/
HBH is an atom compare to that site.
If you just feel like going on an easier site than pulltheplug there is hackits which have harder challenge than here.