Today’s Cooperative Extension organization continues to face challenges of providing relevant, quality programming in urban communities. Challenges include the ability to build capacity in Extension’s urban youth educators to assess and interpret the unique, variable needs of urban clients and to communicate effectively the identified needs to the state land-grant institution to leverage resources. To be responsive, intentional change can be informed and initiated by those closest to the challenges of creating thriving 4-H programs in urban environments – the urban Extension youth educator. Guided by open and sociotechnical systems theory, this multiple case action research study used the critical incident methodology to explore boundary-spanning behaviors of urban Extension youth educators. Four conclusions were drawn from an analysis of the findings including an adaptation of the community-based problem solver quadrant of the Weerts and Sandmann (2010) university–community engagement model. Boundary-spanning behaviors can inform organizational policies related to program development, staff development, hiring procedures, and performance evaluation procedures.