Parole officers are central actors in the penal system as their decisions can affect the timing of a person’s release from prison and also restrict or enable their freedoms in the community upon release. Existing research on parole examines how parole officers think about and govern ex-prisoners via techniques of surveillance, regulation, and support. Few studies, however, provide qualitative insight into how parole officers experience their occupational authorities and associated power over (ex)prisoners’ future, or the emotions generated by frontline supervision work. Using data from interviews with 150 parole officers in Canada, we explore the emotions associated with parole officers’ occupational responsibilities and authorities vis-à-vis the parolee, the public, and the parole officer’s employer. Participants experienced their duty to make decisions that impact their clients’ legal and social futures, and potentially public safety, as a source of emotional stress and concern, as they worried about how their decisions could negatively affect their client, the community, and their own professional status. In illuminating parole officers’ feelings and experiences, we show how parole—the “transition” between incarceration and freedom—produces an emotionally charged experience not just for (ex)prisoners, but also for those engaged in frontline supervision work.