Background: First generation college students, whose parents' highest earned degree is a high school diploma, go on to earn postsecondary degrees less often than their peers whose parents have a college degree. A current approach to addressing this problem is making sure "first gens" are ready to succeed in college. Purpose: There are three extant bodies of scholarship that are potentially useful to researchers and educators who want to think and reason about first gen college readiness. However, leveraging these literatures is difficult because each focuses on a distinct dimension and fails to precisely define its core concepts. The purpose of this study is to coalesce the literatures into an initial framework and, by putting this framework into dialogue with students' lived experiences, synthesize and conceptually clarify the research scholarship underlying the framework. Research Design: In this study, I compare five in-depth qualitative case studies of first gen (n = 3) and non-first gen (n = 2) students who attend the same early college program. I collect data through interviews with the students contextualized by interviews with their teachers and advisors. Using structured, focused cross-case comparisons, I discern in what ways the participating first gen students and non-first gen students do and do not differ in how they (a) conceive of college readiness and (b) experience its development. I then map the students' conceptions onto the framework. Findings: The study's framework brings together from the literature three dimensions for understanding first gen college readiness: (a) student capacities that constitute readiness as well as the ways that (b) educational contexts and (c) students' communities affect the development of readiness. These dimensions fit the experiences of the first gens in this study, thereby substantiating the framework's broad foci. Mapping the first gens' narratives onto the framework also (a) exemplifies how we can think cohesively about all three dimensions and (b) concretely visualizes the core concepts of each dimension. However, research foregrounding first gens' transitions to college raise additional critical questions about institutional conceptions of college readiness and the roles such conceptions might play in shaping first gens' postsecondary experiences. These questions bring attention to: (a) an educational program's cultural norms that first gen students must adapt to; and (b) the ways in which first gen students make sense of their own cultures and identities as they enter into an educational program's culture. Implications: The conceptual ideas captured in the resulting framework have the potential to bracket and focus the work of researchers and educators, pointing them to student capacities, contextual elements, and community factors that can be important to understanding first gens' development of college readiness. And yet, this study also concludes with equally important questions about whose cultural norms drive conceptualizations of college readiness and how colleges can be more culturally and practically 'student ready' for first gens. [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.]