Following trends in entertainment streaming services, online educational platforms are increasingly offering users flexible “on-demand” content options. It is important to understand how the timing of content release affects learning behaviors and firm revenue drivers. The current research studies over 67,000 users taking a marketing course before versus after a natural experiment in which the platform switched the course from a scheduled weekly-release format to an on-demand format with all content immediately available. The switch to on-demand positively impacted short-term firm revenue by increasing the number and proportion of certificate-paying users, suggesting that on-demand content can attract a broader set of consumers who value flexibility. On the downside, the switch resulted in users exhibiting lower lecture completion rates and quiz performance and taking fewer additional business courses on the platform, representing a long-term cost. The results were robust to propensity score matching and stratification. The analyses also revealed that on-demand content enabled learning patterns that deviated from a standard evenly paced schedule, including “strategic” binge learning and stretching out engagement past the recommended course period. Thus, while on-demand formats can boost revenues by bringing in more paying users, managers must consider new strategies for maintaining performance and engagement levels within these environments.