As the cost of college tuition continues to soar, community colleges and state and local governments offer a wide range of access and opportunity programs to best serve low-income and academically underprepared students. In this article, I present a case study of two instructors, both of whom regularly teach Basic Writing courses at the community college, and examine how administrative and financial aid policies, as well as outreach and opportunity program protocol, affect classroom pedagogy and student experience. Ultimately, I argue that these two educators, one part-time and one full-time, successfully navigate the bureaucracy of a complex policy network only through repeated concrete interactions with students and over extended periods of time. Many instructors with lower levels of policy literacy, and especially those novice, part-time, and contingent instructors tasked with teaching in a web of policies, may struggle to best serve Basic Writing students at the community college in ways yet unaccounted for by the field.