<p>Traditional college advising, whereby advisors provide course assignments according to standardized placement test scores, has undergone major transformation in recent years. New placement models, like “informed self-placement” based on multiple measures of documented student achievement, are growing in popularity but remain understudied. To address this gap in scholarship, we took advantage of a unique opportunity presented by statewide reform in Florida to explore how Florida College System advisors described the implementation of informed self-placement and multiple measures between 2014 and 2019, paying special attention to emergent challenges and corresponding solutions. Our findings, drawn from the perspectives of 275 advisors representing 19 different institutions shared during semi-structured focus group sessions, revealed that advisors used a combination of high school experiences, non-cognitive factors, and continued placement testing to inform course recommendations that students could then choose to act upon or ignore when registering for their classes. We also observed several challenges (i.e., increased workload, insufficient information, and student resistance) that advisors managed through group advising, advanced preparation, and self-diagnostic tools.</p>