The work of parole officers who supervise sex offenders rarely comes to the public’s attention unless something goes wrong. Research suggests that those providing postrelease supervision of convicted sex offenders likely experience trauma as a result of their work and that little support is available to respond to their emotional needs. This manuscript explores parole officers’ and parole officer supervisors’ experiences of the symptoms of secondary trauma, defined as the emotional and cognitive experiences of hearing stories that recount one or more traumatic events. The qualitative study described here builds on existing literature by providing a detailed exploration, presented in their own words, of the experiences of specialist parole officers, about how they cope with the symptoms of secondary trauma, and about what they need to help them continue to do the job that the public and the politic want done well. Recognizing and understanding the symptoms of secondary trauma among supervising officers have important implications for maintaining a healthy workforce and for providing effective management of sex offenders in the community.