For universities to accomplish their ‘third mission’, researchers are supposed to engage themselves in problem solving processes with external actors, but to successfully cross organizational boundaries between the universities and the outside world is easier said than done. Rather than developing new collaborative approaches in dealing with practitioners, this paper applies action research as a dual process of participation that elaborates the knowledge exchange process of boundary spanning. Two comparative case studies have been selected because of their similarities in practice and their differences in outcome, making them suitable for studying a researcher performing boundary spanning activities. This study has shown that when contact, negotiation and knowledge exchange have been completed in an effort to advance the change process in the organization and certify preliminary findings in the research process, the researcher has succeeded as a boundary spanner. But to be involved in an organization’s change process and concurrently involve practitioners in the research process calls upon a certain degree of chaos, uncertainty and messiness. This is why boundary spanning activities, such as establishing contact, upholding contact, re-establishing contact, negotiating collaborative terms, and satisfying practitioners’ non-research related demands, take a great amount of time away from conducting research. Hence, this paper argues for the necessity of earmarking university resources to researchers that assume the role as boundary spanners