Using the Education Longitudinal Study of 2002 (ELS:2002), this paper analyzes students' baccalaureate attainment and early labor market performance, comparing 2-year college and 4-year institution entrants and exploring the potential heterogeneous treatment effects of initiating one's college experience in a 2-year college by individual pre-college academic preparation. Utilizing propensity score matching on a rich set of student demographic characteristics, academic and high school attributes, we find that 2-year college entry sharply reduces baccalaureate aspirants' likelihood of earning a baccalaureate, and such negative effects are particularly pronounced for students in the highest quartile of pre-college math ability. In terms of labor market outcomes, female 2-year college entrants are less likely to gain full-time employment, as compared to their female 4-year institution counterparts. We also examine various mechanisms that may hinder 2-year college entrants' baccalaureate completion, including the impact of 2-year college attendance on early academic progress, challenges of the transfer process, loss of credits at the point of transfer, and post-transfer academic shock. Our results provide suggestive evidence in support of all four mechanisms.