Prisons and other correctional settings are spaces often marked by numerous sources of physical, psychological, and emotional insecurity. Researchers have consistently found correctional work to be associated with outcomes such as burnout, posttraumatic stress disorder, and depression. Drawing on open-ended survey questions with correctional workers (CWs) in the province of Ontario, we first identify salient themes in discussions of work stressors and potentially psychologically traumatic events (PPTEs); these include situations involving harm to prisoners, harm to staff, and harms associated with occupational and organizational culture. Next, employing the concept of “habitus,” we consider the social-subjective effects of exposure to PPTEs as revealed in respondent accounts. Key aspects include a disposition of hypervigilance, desensitization, disillusionment, and distrust. We suggest that the CW habitus may, in some ways, serve to mitigate threats in the work environment, though may have negative effects on job performance and well-being, and come to shape social experiences in everyday life.