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Small specialty schools often serve students who were unsuccessful in more traditional academic settings. Serving a disproportionate number of students from historically marginalized backgrounds, these schools are important sites for examining and addressing disparities in educational opportunity. We interviewed teachers at three specialty schools in a mid-sized Midwestern city to understand the possibilities and challenges of enacting educational opportunity in the context of institutional constraint. In line with this year’s conference theme, we conclude with actionable steps that teachers and administrators at small, specialty schools may take to better enact responsive, inclusive, and equitable education when external constraints make it challenging to do so.