In an effort to leverage students’ positive community engagement experiences as they transition to and become alumni, Portland State University (PSU) embarked on a pilot “Continuing Engagement Program.” This article provides a rationale for this effort, an overview of the programmatic elements, lessons learned, and future engagement strategies. The authors situate the Community Engagement Program (CEP) in the current alumni engagement literature, share findings from the PSU program, and hope to inspire additional creative thinking and action to support alumni and other community members’ persistent engagement for positive community change.