Youth UpRising conducted an HIA to inform the the Oakland school board’s planning and implentation of a secondary, specialized learning academy within a low-performing high school in East Oakland. Located in a community with high crime, violence, poverty, and unemployment, Castlemont High School faces disinvestment, decreased enrollment, and a dropout rate of 40 percent. The academy would prepare at-risk students for post-secondary learning and employment opportunities by providing support beyond the school day, including internships. The HIA explored the relationship between the learning academy and educational attainment, income, and related health outcomes. For example, poor educational outcomes and lower wages are linked to a shorter lifespan and higher rates of chronic disease and mental illness throughout life. Higher student dropout rates are also associated with greater levels of crime, violence, and substance abuse. The school district, local community colleges and universities, and the county health department were in support of the HIA, which was conducted with the involvement of five young researchers and support from a working group of local groups that serve the target youth population, including teachers, health organizations, and community residents and government agencies.