Between 2003 and 2006, researchers facilitated a collaborative learning process with representatives of Los Angeles neighborhood councils and officials from city agencies. In two cases, each involving a large city agency, the quality of responsiveness on the part of agency officials to participating citizens was substantially different. This study considers the reasons why agency officials differed in their responsiveness. Using an inductive qualitative and quantitative content analysis across three sources of data, the study develops theory pertaining to bureaucratic responsiveness to citizens in collaborative processes. Specifically, the case findings are generalized to theory through seven propositions for future study. The study’s key finding is that administrator and citizen perceptions of their own and the other party’s roles may influence the quality of responsive behavior in collaborative activity. The propositions identify subfactors or contingencies that may allow administrators to be more responsive to citizens in collaborative processes.