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As equity-centered institutions, two-year colleges contribute to democratizing higher education by providing an affordable pathway to the four-year college for a student population underserved by selective postsecondary education systems. Research shows that 80% of students who start in community colleges intend to earn at least a bachelor’s degree; however, about a quarter of students transfer, and even fewer obtain bachelor’s degrees (“What We Know about Transfer,” 2015). One overlooked roadblock students encounter as they pursue higher education is “gatekeeper” English courses, which are usually prerequired for college-level coursework or program entry and set the standard for college-level writing (Cullian & Biedzio, 2021; Roksa et al., 2009). The stakes of these courses are particularly high for students who speak (and write) nonprestigious varieties of English and those at various levels of English language development and bilingualism, two major groups in the “new mainstream” of higher education seekers that two-year colleges serve (Bunch, 2019). The current sociolinguistic landscape in two-year colleges is unique in that it features academically disadvantaged students who bring rich linguistic diversity to the campus and high educational aspirations. In this context, teachers of English struggle to meet two goals in tension: providing writing instruction that guarantees academic outcomes and ensuring an inclusive environment for underrepresented students, many of whom are first-generation college students working long hours to support their studies and households (Dadgar, 2012; Nomi, 2005). The high cost of remedial education for the state, institutions, and students, and the evidence that students in these courses are less likely to complete their degrees than non-remedial students, has prompted new policies to minimize or eliminate remediation and accelerate students’ placement in degree-credit English courses (Bailey, 2009; Bunch, 2019; Hassel & Giordano, 2015). Despite English teachers’ central role in the pipeline to the four-year college, insufficient attention has been paid to their experiences navigating policy reforms and how these policies impact their decisions in the writing classroom. Utilizing a comparative case study design (Bartlett & Vavrus, 2017a) and drawing on critical sociolinguistics and the anthropology of language and literacy, this study asks: (a) How do preparatory and degree-credit English course instructors interpret and enact the writing standards they are given to work with and those they create? (b) How do they negotiate their beliefs about language and writing standards for college as they do (or do not) adapt to culturally and linguistically diverse students? (c) How do students, particularly those linguistically minoritized, capitalize on their linguistic repertoires and college knowledge as they complete the college writing requirement? The critical role of community colleges in fostering disadvantaged students’ mobility to the four-year college and the growing number of low-income, linguistically minoritized students in these institutions makes this research essential. Ultimately, this study will provide insight for education policymakers and English instructors interested in implementing effective and equity-oriented writing education programs.