Internet security issues often require substantial hands-on training in order to be understood and mastered. The international capture the flag competition (iCTF) is the world’s largest hacking competition that exposes students to real-life scenarios. It tests the students’ ability of both attacking and defending a virtual host that has several vulnerable services within a certain timeframe. Resultantly, students receive exposure, more motivation to excel in their classes while also enhancing their skills. For cyber security competitions to progress efficiently, each component must be thoroughly tested. My project involves testing drivers to evaluate the functionality of any potential service; ensuring proper interaction. By using pexpect, a simple automation and testing tool, I develop scripts to test the ftp services between client and server. These driver programs can be used during the competition to verify students are running their services properly. Pexpect monitors a program’s output and responds as a human would when output matches a certain pattern. Results indicate that the testing virtual machine was not strictly ftp, but ftp-like. Common commands did not always execute successfully, leading to difficult client and server interaction. Other procedures occurred to diagnose the problem for a more successful communication. The competition is expected to provide useful guidelines for educators who wish to organize their own competition.