> But does one go from becoming an expert at breaking systems to automatically churning out a secure cryptographic system? Or does one become an expert at breaking and then build a bunch of flawed crypto systems, as the learning process continues?
Both and neither. Once you get really good at breaking cryptosystems, designing them looks very similar. You start with best practices: use sane primitives (or thoroughly vetted components, preferably!) and put them together in known, simple (simple is key) ways. Then you put on your breaking hat and you attempt to violate every constraint. If you find a flaw, then you iterate or redesign. Once you are happy with it, you start showing it to other crypto breakers, until they're happy with it too.
At this point, you have something that would withstand most basic attacks, and you might be ready to put it out into the world. It's still not battle-hardened and ready for uberconfidential data, but it's in a better state than most cryptosystems. As more and more people look at it without owning it, its trustworthiness goes up, and the risk goes down.
Secure cryptosystems don't pop out of nothing; they're iterative, but not in the "I should do a Show HN" sense. It's iterative like writing a poem -- you don't release it one line at a time.