Creating hopeful possibilities for the lives of men with a known history of perpetrating sexual abuse is perhaps one of the most challenging tasks in the fields of criminal justice and social rehabilitation. Prison in many ways represents the least optimistic setting for such a task. The dangerous and deadening environment of such institutions seems anathema to generating the audacity and vitality required to drive a restorative agenda. The context for this article is a prototypical prison-based sex offender program set in a purposefully therapeutic community. The article recounts a series of uplifting ideas, events, and encounters that inspired often unlikely but productive collaborations among the residents of this community. These events provided the beginnings of an enduring library of stories recounting the valuable and hard-won wisdom attained and shared among inmates, and bestowed upon those still to start the journey.