A qualitative case study approach was used to examine Latino male students and First-Year Experience (FYE) programs aimed at promoting student transfer. Two FYE programs at two community colleges in California were studied: Bridgetown Community College and Portlake Community College (pseudonyms). Study participants included four groups: Latino male FYE students, Latino male FYE alumni, FYE counselors, and FYE coordinators. Data collection strategies included semi-structured interviews, site observations, and document analysis. Analysis of data involved both deductive and inductive approaches, and resulted in identification of four findings critical to the success of FYE programs and their work with Latino males: (a) the need to support help-seeking behaviors, (b) the need to address the "long journey" to transfer, (c) the need to support students' work burden and financial constraints, and (d) the need to incorporate approachable and culturally responsive practices. Overall, the study offers insights into how community colleges might strengthen transfer support for Latino males through FYE programs.