Capture the Flag(CTF) games and competitions have become popular today. Good CTF exercises are not only good approach for learning Cyber Security concepts and techniques in fun, but also useful benchmarks to measure all kinds of popular vulnerability discovering, exploiting, patching techniques or tools. Harder challenges require more sophisticated techniques or tools. On the other hand, the appearance of all the good program analysis tools proposes new challenges for future CTF challenge designers. With the fact that CTF challenges and program analysis tools can complement each other and help each other forward. In this dissertation, we introduce our design method for automated generating CTF challenges.In addition, we propose a new dimension as CTF challenge complexities, which is the ability to resist or obstacle the running of program analysis tools, or referred to as Resistance to Program Analysis Tools.