Objective: In numerous calls for reform to community college math instruction, contextualization has been identified as an effective approach to teaching and learning. Yet, little is known about how faculty contend with math contextualization and how they make decisions about its adoption. This study explored how community college faculty teaching math make sense of contextualization as a result of related professional development, and how faculty make decisions about whether to apply contextualization to teaching math as they make sense of contextualization and other individual or organizational factors. Method: This study adopted a case study approach, drawing upon interviews, observations, and professional development materials from two large, comprehensive 2-year colleges in a Midwestern state. Results: Findings revealed five themes under two main umbrellas: making sense and making change. Three interconnected themes comprised making sense: orientation to contextualization, prior teaching and field experiences, and dual identities as teacher and learner. Two themes characterized making change: external and structural constraints of implementing contextualization and comfort level in operationalizing contextualization. Contributions: This study illuminated the complex process of faculty sensemaking of math contextualization, and how this sensemaking, in light of individual and organizational factors, shapes their decisions around math instructional change.