First-generation and low-income students in the U.S. are attending four-year colleges and universities at unprecedented rates. This demographic shift comes, in some part, from initiatives adopted by many universities aimed at reducing structural barriers to college access, such as eliminating student loans in favor of grant-based scholarships. These improved educational opportunities for low-income students are considered by social scientists to be among the most powerful methods for stimulating upward mobility and decreasing the negative impacts of poverty. Yet, as I show, the traditional reduction of mobility to economic outcomes in the social sciences overlooks how “becoming” upwardly mobile is a social and interactional process. Drawing on in-depth interviews and participant observation with 150 students attending elite colleges and universities in four major U.S. cities, I argue that first-generation and low-income students experience a consequential double bind in their college careers. Their ability to be a student in these elite settings demonstrates their dedication and commitment to social mobility – often motivated by their desire to be able to give back to their families and lower-resourced communities. Yet, as they progress in college, they must balance the personal and social transformations that college can bring with their histories and ties to home. Unlike their classmates from more privileged backgrounds, these students feel competing pressures to “buy in” to the elite educational context without “selling out” in the eyes of their home communities. Navigating this double bind can negatively impact student outcomes, campus engagement, and ties to home. Paying attention to the power of social beliefs and relational ties reveals that upward mobility is best understood as an experiential and longitudinal social process – a process that must be considered alongside conventional notions of economic gain when approaching questions of social mobility.