Objective: Despite the fairly substantial body of literature devoted to understanding whether dual enrollment programs are related to academic success in college, less is known regarding how dual enrollment transmits its potentially positive influence, especially among two-year college students. In this study, we fill this gap by delving into the process of how dual enrollment is related to academic success among students attending two-year technical colleges. Specifically, we examine academic momentum as a potential mediator of the relationship between dual enrollment and educational outcomes. Methods: We draw on a sample of more than 15,000 first-time postsecondary students who entered Wisconsin’s two-year technical colleges in 2009 to 2010 after graduating from high school between 2007 and 2009. Using a path analysis, we investigate student transcript records, along with data from the National Student Clearinghouse. Results: Participation in dual enrollment is found to be related to more attempted credits, higher likelihood of college entry without delay, summer enrollment, as well as stronger academic performance. These early academic momentum indicators are then positively related to students’ college completion or retention, fully accounting for the positive relationship between dual enrollment participation and college outcomes. Contributions: Our study provides a finer look into two-year college students’ academic progress and success and how dual enrollment may fuel this process by promoting students’ academic momentum early during their college careers.