This Note considers the constitutional implications and policy concerns arising from the updated compassionate release mechanism. Part I of this Note traces the statutory development of compassionate release in the federal prison system. Part II examines the place of compassionate release within the federal constitutional scheme. Part III turns to the policy concerns surrounding representation by appointed counsel of compassionate release petitioners. Finally, Part IV proposes expanding the guiding definitional boundaries of compassionate release and concludes by arguing for an independent body in the executive branch to handle administrative compassionate release petitions.