This article presents a 2-year critical case study of an urban high school innovating to enhance the academic performance of low-income Latina/o students, highlighting high-leverage practices that promote boundary crossing between school and community. First, we highlight foundational elements of school logic, mission, and community ethos that enabled boundary crossing. Second, we identify a key set of boundary-crossing practices that tap and build community wealth, and forms of capital that are shared, by bringing community into school and fostering youth engagement in community. We also reveal opportunities afforded and complexities arising from boundary crossing between school and community.