This article presents findings from a participatory evaluation of alumni groups--Think Tanks--affiliated with the Inside-Out Prison Exchange Program. Think Tanks are cocurricular settings wherein participants develop and apply skills and capacities valuable within and beyond the context of meetings. Data come from nine focus groups convened in eight prisons located in five states. The article addresses the dearth of information about cocurricular programs in prison and outlines why they are important settings for professional and personal development. The analysis focuses on participants' concerns about their cocurricular program. Four themes emerged that indicate the relevance of structure, culture, and agency for cocurricular programs in carceral settings. Themes of concern include the following: challenges with the ability to convene, group consequences due to individual member misconduct, limited resources, and group disruptions from new member additions. The findings have implications for inquiries that assess practices that affect education prison program participation and engagement. Findings also suggest the need to complement curricular with cocurricular programs in carceral settings to advance maximum participant benefits in prison and postrelease.