The Sacramento Tree Foundation (Tree Foundation), a nonprofit organization operating in the greater Sacramento California region, has been engaged in planting native oak trees in urban and suburban areas since 1998. Through an effort to provide efficient access to tree mitigation services and support compliance with local tree protection ordinances, more than 20,038 trees have been planted, monitored and cared for. Through developing the program and building hyper-local best practices, Tree Foundation staff has achieved a very high rate of success, growing the program to include a broad variety of reforestation, habitat restoration, habitat creation and urban forestry services. As urbanization continues to spread into our oak woodlands, reforestation and habitat enhancement of disturbed open space, urban edges and waterway corridors will support conservation of habitat and species. Successful methods of managing tree establishment issues will increase project sustainability and maximize the cost effectiveness of this work.