Security-based “Capture The Flag”s are really, really fun. I found SmashTheStack I/O, a typical wargame run by some terrific (and very intelligent) people. I wanted to be able to build my own environment for such wargames, and ended up spending a few hours yesterday writing ctf-bootstrap. It sets up users, levels, and any code that you have in a specified directory. I’ll eventually get around to writing longer documentation, but for now, scan the code if you’re interested.
 They also run a very welcoming IRC channel over at #io on irc.smashthestack.org.
 Open-sourced at https://github.com/siddarth/ctf-bootstrap