It's not common to find Ruby problems in security CTF (Capture The Flag) competitions, but luckily there are some out there. These type of problems are always a great opportunity to learn some Ruby internals or features of the language that aren't usually known. They are also a perfect excuse to do crazy things and get as creative as possible. In this talk I'll present some problems from the CTF organised by a famous Japanese security group in 2016 and some ways to solve them.