This dissertation inquires into how learning to write under the system of state standards and standardized tests in U.S. K-12 schooling affects student writing development in college. Research literature has documented how the state standards define writing, as well as how they shape teacher action, but not how these concepts of writing shape students’ long-term writing development. To trace standards to teaching to students, I conducted a comparative case study of four student writers finishing their first year of university writing, learning about their experiences writing in both high school and college through discourse-based interviews. Then, I interviewed their high school teachers and principals to learn about how the learning experiences the students described were — or were not — structured by the standards system. Through the lenses of Driscoll and Zhang’s theory of writing development and Tyack and Cuban’s concept of the “grammar of schooling,” my qualitative data analysis finds that standards did not fundamentally structure these teachers’ goals or strategies for writing instruction. And yet, the students still had these concepts of school writing as a rule-governed, rote exercise, attributing this sense to their need to fulfill grade expectations. I then argue that the issue facing U.S. writing instruction is not the standards and tests, it is the structure of school itself — how the mechanization and scoring of learning closes off opportunities for productive failure, experimentation, and reflection. Policy remains an important part of this ecosystem, as teachers and administrators rely on the standards system for assessment and marketing purposes. As long as the accountability structure relies on testing (a metric that cannot inquire into students’ decision-making process), the critical elements of writing development where these students need the most support will remain outside the incentive system that governs our schools. These findings suggest that writing instruction should include conversations about the grammar of schooling in order to heighten students’ awareness of these structures and their agency within them. From an administrative and policy perspective, writing studies must search for ways to align student, teacher, administration, and public definitions of writing development.