This study describes how a group of teachers in a US public school developed and used permission-seeking moves as strategic and agentic tools to change their school curriculum and challenge norms of teaching. Although the notion of asking permission is typically considered disempowering in educational contexts, this study demonstrates that certain forms of permission-seeking (and giving) can foster collaboration and teacher agency across multiple constituent groups in a school community. This 2-year ethnographic study occurred within a context of a test-driven teaching environment with shifting student racial and economic demographics. Our research offers a reconceptualized theory of permission within a teacher agency framework and new possibilities for practitioners to engage in transgressive teaching with diverse learners in hyper-standardized teaching contexts.