Approximately 1-in-3 students on American college campuses come from families who have little to no experience in higher education. Despite their growing presence, many potential first-generation students, those without a parent who has completed a bachelor's degree, will never set foot on a college campus, and those who make it face significant adjustment and persistence challenges. Research on first-generation students has overwhelmingly portrayed this student group as uniformly disadvantaged when it come to gaining access to and achieving success in college. As a result, these students have become the target of pre-college support programs and practices that aim to improve college preparation. Critical to improving the access to and success in higher education for first-generation students is a high school environment that encourages and prepares students to pursue a college education. More specifically, studies have shown that a high school's college-going culture can have a positive impact on students' aspirations and college-going rates. Conceptually, college-going culture is useful for exploring the pathway to higher education faced by first-generation students, particularly as these students rely heavily on the school for support and guidance. However, research on college-going culture has not focused extensively on at-risk students and their aspirational development. This study follows 23 low-income, first-generation students across seven high schools in Missouri. Relying on longitudinal, qualitative data I explore how first-generation students experience the postsecondary aspiration and decision-making process in different college-going culture environments. Contrary to the majority of research on first-generation students, I find distinct variation in how these students approach and experience the postsecondary process. I argue that first-generation students fall into three distinct, yet fluid, categories based on their relationship and engagement with school, their approach to academics and the college process, their system of social supports, and their knowledge of and connection to their future aspirations. I find that the different types of college-going cultures interact with and influence these student categories in important and complex ways by providing varied levels of resources, support, and exposure to postsecondary opportunities. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]