Parole officers (POs) support rehabilitation and desistance but face mental health challenges and occupational stressors. Parole Work in Canada provides novel insight into the occupational routines, mental health impacts, and identities of this oft-overlooked group of correctional workers. The authors conducted 150 interviews with POs employed in Canada’s federal correctional system and traverse prison and community spaces in their analyses. They also examined how workplace culture and relationships affect POs’ well-being, provide implications for occupational routines created by COVID-19; interrogate organizational structures, culture, and practice; and unpack how POs understand carceral space, self-presentation, and the tensions between supervising and supporting criminalized people.