In university, successfully challenging also gives you credits for that course (though there is a small fee per unit). I successfully challenged four courses (all in graphic design) - three of which were based on portfolio review and the fourth was based on completion of course projects in an accelerated period. Additionally, though not quite a challenge, I was able to speak with a couple CS professors and get them into admitting me into their courses despite not having the prerequisites (though was doing them concurrently).
The course requisite structure is more a guideline than a rigid computer system that works one way and only that way.
One of my friends was able to skip 61a by meeting with the department chair, Paul Hilfinger, and convincing him that 61a would be a waste of time for him. My friend could drone on and on about the simplest of subjects so we assumed he just annoyed Hilfinger until he said "enough already".
(I skipped the first two intro CS classes in college after talking to the professors and figuring out the right place to start given my background.)