This study explored how managers of outlying audiences span the boundaries between sponsoring institutions and the audiences they serve. The three primary research questions guiding this action research multi-case study were: (1) What strategies do urban 4-H youth educators use to navigate resistance from both the urban community and the rural-oriented Cooperative Extension system? (2) What behaviors do urban 4-H youth educators use to span boundaries for the Cooperative Extension system and for working within the system? and (3) What is the impact of action research at the individual, organizational, and national policy levels related to boundary spanning behaviors of community-based, urban 4-H youth educators? Through action research the principle investigator, along with urban 4-H youth educators from eight states identified as urban programming exemplars, identified boundary spanning behaviors of educators who sustain programs in urban communities. Data were collected through interviews with organization leaders, urban youth educators, and from researcher observations throughout the study. The action research interventions included identifying critical incidents in urban youth education and consulting with policymakers. Three conclusions were drawn from an analysis of the findings: (1) As a subculture of self-directing urban youth educators, educators use informal learning to manage internal and external resistance; (2) The boundary spanning behaviors of assessing, engaging, reformulating and advocating were categorized in an adaptation of the community-based problem solver quadrant of the Weerts and Sandmann (2010) university-community engagement model. These behaviors link the sponsoring organization and the outlying audience; (3) Identification and acknowledgement of boundary spanning behaviors used by urban 4-H youth educators hold potential for learning at individual, organizational and national policy levels; and (4) Technology, with limitations, can facilitate action research with geographically dispersed participants. Implications include the following: (1) Knowledge and information gathered by boundary spanners engaging with outlying communities to structure relationships, initiatives, programs and collaborations illuminate the complexity of communication between organizations and external clients; (2) Boundary spanning subcultures model the potential for organized communities of practice; (3) Boundary spanning behaviors can inform policies related to program development, staff development, hiring procedures and performance evaluation procedures; and (4) Action research serves as individual professional development and potential organizational learning.