How can universities ensure that the first-year learning experiences are purposeful, personal, and transformative? This study explores challenges post-secondary institutions face in the ever-changing landscape of first-year teaching and learning. It spanned 18 months and included surveys, reflections, and an environmental scan of 92 first-year course syllabi. The study captures the perspectives of faculty, staff and students, in both first and second year, in relation to their academic experiences, and includes recommendations for supporting both student retention and teaching and learning experiences.