Authentic learning requires free thought—curiosity, inquiry, imagination, initiative, problem-posing, question-asking. Learning is undermined when students are inspected, spied upon, regulated, appraised, censured, measured, registered, counted, admonished, checked off, prevented, and sermonized. In this episode, we visit a unique college commencement ceremony—filled with joy and pain—and explore with the Prison + Neighborhood Arts/Education Project and University Without Walls what it means to stay all the way human inside an institution built on dehumanization, and to face fully the contradiction of teaching for freedom in spaces that demand passivity and obedience.