People use behavioral heuristics, aka mental shortcuts, to make 35,000 predictions a day, and engineers use heuristics to develop complex algorithms overnight. Throughout this presentation, I’ll demonstrate how I use behavioral science research to identify Active Directory misconfigurations, target confidence in fragile systems, and create strong narratives in order to bypass security controls. After establishing that offensive tradecraft reflects the cognitive limitations in our decision-making abilities, I will use red team recommendations to question routine habits and encourage rational thinking.