Cultivating interdisciplinary connections between freshman and capstone students epitomizes a novel pedagogical approach to deepen student understanding of the learning process in a Community College environment. Within such a context, this article focuses on the outcomes of a two-semester collaborative effort that aims to establish and strengthen interactions between students at opposite ends of the academic spectrum. The work discussed focuses on an initiative in which capstone students in their final college class before graduating are supported in using their educational experiences to guide their first-year peers as they make the transition to college life. After discussing the creation and implementation of scaffolded collaborative assignments in which capstone students peer-reviewed freshman students work, the paper assesses the impact of the research on student understanding of the learning process by analyzing the quality of their work in the peer-review endeavor and the outcomes of their self-reflection activities.