Although learning is the foundation of improved policymaking, little is known about policy learning in transportation programs. To address this knowledge gap, this article explores how two structural factors – (1) restricted information dissemination through centralized decision-making structures and (2) high senior civil servant turnover – affected policy learning in Colombia's road concession programs. Using a case-based research design, our analysis indicates that centralized decision-making structures and high senior civil servant turnover impeded policy learning in Colombia's first three road concession programs. Conversely, the absence of these factors in the fourth program led to policy learning and improved programmatic outcomes.