University–community partnerships have long sought to develop interventions to empower historically marginalized community members. However, there is limited critical attention to tensions faced when community engaged courses support urban planning initiatives in communities of color. This article explores how three Florida State University planning classes sought to engage the predominantly African-American Griffin Heights community in Tallahassee, Florida. Historically, African-American communities have been marginalized from the planning process, undermining community trust and constraining city planning capacity to effectively engage and plan with African-American community members. In this context, there are opportunities for planning departments with relationships in the African-American community to facilitate more extensive community engagement and urban design processes that interface with broader city planning programs. However, mediating relationships between the community and the city within the context of applied planning classes presents unique challenges. Although city planners have increasingly adopted the language of community engagement, many processes remain inflexible, bureaucratic, and under resourced. Reliance on inexperienced students to step in as community bridges may also limit the effectiveness of community engagement. Thus, while community engaged courses create opportunities to facilitate community empowerment, they also at times risk perpetuating the disenfranchisement of African-American community members in city planning processes.