Service learning as a pedagogy and its partner, community based research, have both made productive interventions into prison and jail life, greeted many times with relief by administrative staffs no longer funded for what some politicians call the “extras” of education. From the inside, administrators and inmates join those on the outside—ex-inmates, educators, concerned family members, students and other citizens—to stimulate intellectual and practical engagements between the separated communities that prison engenders. Many of the activities and programs discussed in these pages have started new conversations that reach beyond the walled and barred “homes” of the incarcerated.