We sought to understand barriers and facilitators to academic engagement among student parents at six community colleges, through in-depth interviews with student parents, staff, and faculty members (n = 49). Using a grounded theory approach, we found parents were expected to repeatedly self-advocate and request accommodations such as for extended childcare hours, food subsidies, and assignment deadlines. This burden was either constrained or relieved by 1) student parents' strengths and strategies, 2) campus structures and groups operating collectively or in silos, and 3) the way faculty, staff, and campus programs responded to student parents' needs. Community colleges can reduce the burden on students to request accommodations by presenting clear policies, streamlining resources to student parents directly, and normalizing their use.