Pedagogy can be a humanistic way of engaging social realities in the current era of persistent social marginalization, racial injustice, and political polarization. This article explores one particular community-based pedagogy known as Inside-Out, which brings incarcerated students together with students from a college campus to study together at a local prison or jail. From the student and instructor perspective, the article looks at the ways that Inside-Out catalyzes humanistic thought and action—from within the social-historical context of prisons and universities. It explores how, if processes of racism or criminalization position social groups against each other, a humanistic pedagogy has the potential to meaningfully bring people together across social divides to reckon with dehumanizing social realities. Conclusions are offered on some key elements of an Inside-Out pedagogy that embody a humanistic approach and are relevant to other pedagogical contexts.