Objective: Few community college students who aspire to transfer ever do so. Prior research suggests that relationships with advisors, faculty, and administrators may play an important role in promoting successful transfer outcomes, particularly for traditionally underserved students. This study examines how students identified and weighed possible transfer destination colleges, and how dedicated and personalized advisement shaped students’ transfer plans and contributed to their transfer outcomes. Method: This mixed-methods study uses interviews to explore students’ transfer planning processes, as well as student record data to examine transfer outcomes. Analyses compare students who received personalized transfer advising through a community college honors program and similarly qualified transfer-aspiring peers attending the same six community colleges who received “business as usual” advising. Results: Findings suggest that personalized advisement and relationships with transfer advisors contributed to higher rates of transfer and may support transfer to more-selective destinations. Contributions: This research extends the literature on community college transfer by tracing students’ planning processes, exploring factors that raise or lower transfer aspirations, and estimating the effects of an advising-intensive honors program on students’ transfer outcomes, including the selectivity of their transfer destinations. We also offer more empirical support for the importance of personal relationships and transfer agents in facilitating successful transfer outcomes.