Students are coming to school with myriad issues that teachers and schools cannot address alone. ecological systems theory posits that the environments with which a child comes into contact, either directly or indirectly, can impact her or his development (Bronfenbrenner, 1979). With the support of community partner organizations in the local community, community schools can effectively respond to students’ needs and help them navigate the interconnected web of environments. Through interviews, focus groups, and a document review, this cross-site case study explored the practices that are employed by community school leaders (school staff and employees of community partner organizations) at two pilot high schools in the Los Angeles Unified School District (LAUSD), to implement six guiding principles of community schools. The study also captured impacts of these practices through participants’ perceptions, documents, and the application of transformative leadership theory. The findings revealed that the pilot school model is a natural avenue for the community schools strategy, and that intentional practices and a shared vision by all stakeholders can result in transformative impacts on students and the school as a whole. District and school leaders could consider developing processes and systems for implementing a community schools strategy district-wide by providing funding for community school coordinators for school sites, working with school leaders to develop their shared decision-making skills, and leveraging the assets and resources of community partners.