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Recent media reports have attempted to shed light on correctional officers who end their careers in disgrace for either having sexual relationships with prisoners or for smuggling contraband into correctional facilities. In this paper, I take an autoethnographic approach, reflecting upon my seven years as a “guard-researcher” and demonstrate through real-life examples how inmates identify the weak links among prison employees, subtly feel them out, and then untiringly persist in establishing these inappropriate relationships. This article shows how seemingly benign gestures of inmates are actually calculated moves taken to gain leverage and exploit their marks, the weak correctional staff members who fall for these tricks.