Capture the Flag (CTF) competitions have attracted an increasing interest over the last decade. They proved to be an effective tool employed in academic, professional, and military contexts to teach practical IT security topics, as well as to strengthen lateral thinking skills and to acquire hands-on experience in the field. This talk will give you an insight into the various challenges that a team has to face while playing an attack and defence competition by leveraging on the experience gained by mhackeroni. We will report on the infrastructure developed by the Italians to clash with the world's best teams at DEF CON CTF and present some concrete examples from well-known hacking competitions.