Two-year colleges have served as vital stepping-stones for students seeking to earn a bachelor's degree. To achieve that goal, these students must complete their current program's requirements and then matriculate at a four-year college--a process known as "vertical transfer." This is commonly extolled as a cost-saving strategy, but it can also create unexpected challenges for students. Yet relatively little is known about how vertical transfer may affect students' future labor market outcomes. To shine light on the vertical transfer process, this report compares the outcomes of otherwise similar groups of students who aspire to obtain a bachelor's degree, with the only difference being that one group begins college at a two-year college, while the other begins at a four-year university. We also stratify our sample to study if the effects of initiating college at a two-year institution differ across various student populations. The report concludes by examining several potential explanations for the disparities between students who initiate at two-year and four-year colleges. These include a slower accumulation of credits and early academic progress, challenges during the transfer process, a loss of credits at the point of transfer, and post-transfer academic shock. In this regard, two-year institutions may not be the stepping-stone that many policymakers and families have hoped for, unless additional efforts are made to improve the transfer pathway.