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I bet that Thomas and Patrick could do something like have dynamically created tests, where there are multiple versions of an exploit, so that they test the same skill but in different ways. You might have a challenge that tests whether you can do SQL injection, but the tables may differ. Overrunning a buffer (as Patrick mentioned in his post about Microcorruption) could depend on different payloads.

I naiively believe that things could be varied enough that you would need to understand the concepts rather than paste answers, in which case "cheating" would mean "learning", and is basically something they say they want you to do. I'm not sure how hard it would be to get to that point rather than being vulnerable to Bob the Super Coder posting walkthrough screencasts, but I trust that the founders are already savvy enough to have been thinking about that.

Unfortunately, I suspect you overestimate the obfuscating power of dynamic content when the number of users is sufficiently large.

A certain MMO I play recently had a limited-time event built around figuring out the meaning of different clues (locations to go to for the actual meat of the event), and despite a fairly large number of variations, people had collectively figured out just about every possible clue->location mapping within a matter of hours.

That's not to say you can't prevent cheating, but that even with relatively little incentive (that whole clues thing gave only a single cosmetic item, and anecdotally I've seen very few people actually use theirs) users can and most likely will outpace any attempt to prevent it by means of varying the problem.

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