At the turn of the 20th century, the Philippines’ colonization by the United States ushered in the introduction of an American-run public school system conducted entirely in English. This dissertation centers the voices and perspectives of Filipino student writers in the American colonial classroom by analyzing a corpus of essays produced by high school students in Lucena, Philippines between 1904 and 1907. Through archival and qualitative inquiry, I develop echoing + resistant imagining as a rhetorical strategy that accounts for the necessity for colonized writers to placate colonial expectations of “good” writing and “good” colonial subjecthood and to also engage with anti-colonial resistance. By analyzing student writing produced under American colonial education, as well as historically locating this analysis in archival research on the Filipino student experience, this project adds texture to the historical conversation on writing, imperialism, and the Filipino colonial experience and, more broadly, to the role of English and writing in imperialism. Listening closely to colonized student writers shows that writers who are racially, ethnically, and politically marginalized innovate remarkable strategies of rhetorical savvy to write against the dominant discourse. My analysis shows that Filipino student writers simultaneously replicated discourses of modernity, progress, and rationality and also articulated desires for agency, community, and social change. By exploring the roles that students played, and were asked to play, in debates over Filipino fitness for independence, I highlight the contradictions and double binds that students navigated while composing essays under the colonial gaze. For example, amidst heated public debates on Filipinos’ intellectual and moral fitness for liberal education versus industrial education, Filipino student writers claimed, in their essays, that they saw education as a tool for advocating for rights and justice. Thus, Filipino student writers echoed and affirmed notions of the Filipino student as an eager and grateful beneficiary of colonial education, while also expressing dissatisfaction with a highly stratified colonial society. Ultimately, my project offers a transnational and postcolonial perspective that accounts for the role of colonization on student writing and also develops a historically and culturally informed theory of rhetorical production.