In the current chapter, I examine how gender is understood based on my experience as a woman undergoing the Correctional Training Program. I reveal how the environment instills values, some consistent with masculinities and some femininities, but all encouraging confidence, stoicism, and communication. Thus, I counter the notion of prison or the Academy, as an always hypermasculine workspace and instead unpack the diversity the Academy requires to meet the multiple functions expected of correctional officers. I reveal how the hegemonic ideal in the Academy values composure, ability, and work ethic. Nonetheless, I reveal through experience how the primary function must always start with security, understood as the preservation of life through physical health, and how without life there is no possibility for psychological or social health, although all are valued.