Social work's weak presence in the field of corrections is peculiar, given that those involved in the criminal and juvenile justice systems are undeniably among the vulnerable and oppressed populations that the profession has traditionally served. The field of juvenile probation shares roots with the profession of social work but lacks a strong connection to it today. Traditional explanations focus on the reluctance of social workers to engage clients in coercive environments, but historical analysis suggests that this account tells only part of the story. An examination of social work's origins shows that issues involving gender stereotyping and the failure of theory help explain social workers' diminished role in juvenile probation. In recent decades, changes in attitudes regarding gender and working with coerced clients, as well as evidence of effective interventions, suggest that social workers may be ready to reengage meaningfully with juvenile probation and other corrections work. This article outlines steps in professional education and workforce development that would move the profession toward reintegrating social work into the corrections field.