In recent years, numerous scholars have become disillusioned with first-wave critical pedagogy, particularly the idea that transformative intellectuals can emancipate students and advance progressive politics despite working for reactionary educational institutions. Portraying social justice-oriented teachers as dogmatic, naïve, and self-contradictory, these postfirst-wave scholars hope instead to cultivate students’ critical literacies within the default and privatized ethos of the American Dream. A handful of other scholars look to literacy education’s progressive extracurriculum for ideological refuge from institutional hegemony. This essay, while agreeing that significant obstacles constrain progressive teaching in ways that first-wave critical pedagogues have not sufficiently acknowledged, nevertheless rejects the idea that progressive teachers are trapped by unavoidable paradox. It argues further that, rather than accentuating a dichotomy between institutional and extracurricular, socially conscientious teachers can more productively negotiate the challenges of progressive education by breaking down walls between these locations.