This qualitative single-case study examined the institutionalization of community engagement at a selected land-grant university by melding individual and organizational perspectives and examining the process as an adaptive challenge. Specifically, the study applied Holland’s (1997) assessment matrix for institutionalizing community engagement and Weerts and Sandmann’s (2010) boundary-spanning framework. Thematic analysis and constant comparison were used to examine data from transcripts from open-ended survey questions, focus groups, and semistructured interviews. Findings showed that institutionalizing community engagement represented an adaptive challenge that required a critical mass of boundary spanners enacting a variety of roles inside the university. Three conclusions resulted: (1) The case institution created conditions for personnel to safely experiment with community engagement; (2) the university engaged in strategic thinking and planning around the sustainability of community engagement; and (3) in its institutionalization efforts, the case institution fostered an “adaptive braid” model encompassing organizational and individual actions and motivations.