Auburn University has made considerable strides in faculty engagement in outreach initiatives. This progress is in part due to a revision of the faculty handbook that includes outreach as one criterion by which faculty can be assessed for promotion and tenure. This article examines one art professor’s experiences engaged in the Alabama Prison Arts + Education Project (APAEP). Her experiences suggest that departmental support and college leadership, in addition to policy changes, significantly influence the ability of faculty to remain engaged. Moreover, this professor’s experience suggests that faculty engagement in outreach initiatives positively influenced the learning experience for APAEP students and Auburn University students, as well as the faculty member’s pursuit of promotion and tenure.