Comment by gmluke

This is slightly tangential since you specified a conspirator on the inside, but how easy is it to break a homegrown encryption algorithm if you don't have the source code? I assume there are tools (what are they?) that will break a simple caesar cipher if you have more than a sentence or so of plain text to work with. But if you strung together 2-3 broken algorithms and your attacker doesn't know which ones, is it still trivial to decrypt?