This article examines the pervasive difficulties experienced by first-generation students in their quest to attend postsecondary settings. A change in the profile of the undergraduate student body has changed dramatically with respect to first-generation students’ age, enrollment status, and family conditions. These students are likely to enter college with less academic preparation and have limited access to information about the college experience. Low-income, minority, first-generation students are especially likely to lack specific types of college knowledge, which includes knowing how to finance a college education and complete basic admissions requirements. For these students to be successful, it is imperative to understand the pervasive obstacles they may encounter. The article identifies the challenges that first-generation students experience and their perceptions regarding the postsecondary experience, and it concludes with recommendations for successful academic practices.