The first part of this article situates and describes the conceptualization, implementation and 'success' of a project--an alternative high school for formerly incarcerated men and women--within the flourishing prison industrial complex in the United States, a structure that disproportionately impacts poor people and/or people of colour. The second part, snapshots/ stories to break your heart offers two anecdotal "emotional striptease" ( Fusco 2001 ) moments from the start of this project to illustrate the complexities that have arisen, or, simply, the need to do more. Finally, a brief postcript, outstanding in our field? that queries how I (and others in this project) struggle with negotiating the university/community relationships and the 'hero' trap.