This article draws on a five-year mixed methods study and focuses on the way staff tailor support within a comprehensive college transition program to meet the needs of low-income, first-generation, and racially minoritized students by adapting programmatic offerings and requirements to fit students' multifaceted needs. The study also identifies the way tailoring reduces cognitive load for students because the tailored interventions are embedded within a single program, rather than having students visit dozens of offices trying to piece together the support they need. The program created an approach to tailoring student support that draws on the best of predictive analytics and case management simultaneously while also being non-deficit and asset-based. Our study contributes to the literature by identifying the value of tailoring approaches to address students' multiple needs and identities.