This study examines a Detroit suburb experiencing an unexpected influx of working class African American students. Dilemmas engendered a cultural mismatch between teachers and students. In a controversial climate where students cross the boundary line in search for educational parity, this study examines a seventh-grade English teacher who enacts code-switching pedagogies. This study also examines the perspective of two African American focal students from Detroit, as they negotiated their identity in standard and nonstandard writing contexts. Ultimately, this study presents an argument that teachers must facilitate appropriate contexts for standard and nonstandard writing conventions for all students. (Contains 7 figures.)