Often without guidance in completing college-related tasks, first-generation students face unique challenges during the summer before college. This case study investigates this critical time period by studying a cohort of 33 newly graduated students from the same urban, public high school. Guided by social capital, college readiness, and "nepantla" frameworks, results shed light on students' barriers and pathways to transitioning to postsecondary education. The authors call for an extension of college readiness frameworks to the summer before college and also problematize the notion of a college-ready student.