The Jefferson High School Modernization Project represents an almost $300M investment in Portland, Oregon’s historically Black high school. After more than two decades of economic displacement, many of Jefferson’s multigenerational families now live far from the campus but maintain deep connections with the school. The School District and the Black community is keen to maintain the legacy of the school while also planning a state-of-the-art facility that is equitable with other recent modernization projects in the city. Using the lens of Design Justice, a unique community engagement process is changing the way Portland Public Schools is listening to its stakeholders; the process is directly influencing the Education Specifications and the design goals for the project. This presentation will share insights and lessons learned from this engagement effort with the aim to inspire others to lean into this sometimes-messy, often-complex, and ultimately deeply rewarding way of working with the most marginalized and underrepresented voices of our community.