In the spring of 2017, the "Harvard Educational Review" ("HER") published the first part of a symposium on the intersection of incarceration and education. That collection of articles offers scholarly perspectives on the purpose, challenges, and potential of education in carceral settings, as well as the origins and consequences of the carceral system. To continue the conversation, the editors sought out the voices and expertise of those who work at the nexus of education and incarceration. As such, "HER" sought to identify practitioners whose work bridges the two spheres and held interviews with four leaders and innovators in this space. HER editor Simone A. Fried prepared interview questions, and editors Krista Goldstine-Cole, Celia Reddick, and Lauren Yoshizawa conducted the interviews. Each conversation was digitally recorded and later transcribed, then edited and condensed into the narratives presented below. These four interviews illuminate the promise and possibility, as well as the challenge, of educational practice in the context of incarceration and its effects. Jody Becker, the secretary of Washington State Department of Corrections, reflects on the consequences of parental incarceration for children, highlighting the agency's strategic commitment and practical efforts to enhance educational opportunity for both generations. Barbara Carr, Juvenile Court administrator in Jefferson County, Washington, enumerates the growing effects of evidence-based programming in juvenile courts and, in particular, the increasing role for probation counselors as educational advocates for youth in the justice system. Gillian Knapp, a professor of astrophysics and one of the founders of the Prison Teaching Initiative at Princeton University, looks back over eleven years of teaching science and mathematics in New Jersey prisons. By focusing attention on the impact of learning math on educational choice and competence across the curriculum, Knapp reminds us that everyone should receive a decent education. Finally, Luis Giraldo, director of Equity, Diversity, and Cultural Competency at Santa Barbara City College, shares stories from his work at Homeboy Industries. Giraldo pushes us to hear, understand, and respond to the "invisible needs" of previously incarcerated and gang-involved individuals as they transition to being students.