From 29 October to 14 November 2021, the Centre for Strategic Infocomm Technologies (CSIT) ran The InfoSecurity Challenge (TISC), an individual competition consisting of 10 levels that tested participants’ cybersecurity and programming skills. I took away important lessons for both CTFs and day-to-day red teaming that I hope others will find useful as well. What distinguished TISC from typical CTFs was its dual emphasis on hacking AND programming - rather than exploiting a single vulnerabil...