“College readiness” has become a national buzzword in light of efforts to improve high school students’ ability to successfully transition into postsecondary settings. One component of this transition that has long been an area of concern is students’ readiness for college writing. Numerous stakeholders have weighed in on the question of what will improve students’ writing readiness, but few studies have considered the perspectives of students as they write in both high school and college. This dissertation addresses this gap by contributing an ecological, multi-layered perspective on how student writers develop as they become college-going adults. By taking into account the role that multiple systems play in this development, this study examines the interwoven contexts that shape writing and writing development. To that end, I used discourse analysis and qualitative research methods to analyze a variety of data sources, which included policy and curricular documents, field notes from classroom observations, and transcripts of teacher and student interviews. The study focuses on three components of the transition from high school to college writing. First, I identified how writing and college readiness are conceived in policy and curricular documents, and I describe how differences between these documents might impact students’ development as writers. Building on these analyses, I then examined the instruction that occurred within two high school language arts classes, an Expository Reading and Writing Course and an Advanced Placement English Literature and Composition course. I found that the teachers’ beliefs and practices reflected some of the ideologies present in the curricula they used and resulted in differences in the kinds of instructional activities they emphasized. Finally, I examined the developmental trajectories of twelve student writers as they moved out of their shared high school environment into a variety of postsecondary institutions. Students’ experiences revealed three different trajectories that reflected the extent to which they developed in their writing and/or their relationship to writing. Four components may have contributed to the kinds of trajectories that emerged, and these components suggest areas in which high schools and colleges might consider implementing practices that will help support students during this transition period.