Most college readiness reforms in high school focus on academic preparation for college, while underprepared students who do not intend to enroll in college are often left underserved. Using a unique source of data from essays written by students, we examine the role that high schools play in supporting students who test below college-ready in developing their postsecondary plans. Our findings explore how helpful high schools are to these underprepared students, the characteristics of helpful high schools, the types of resources and supports that students find helpful, and students' recommendations for improving the planning process.