A transcribed conversation between a mathematics educator and a disability studies educator is presented to highlight cross-disciplinary dialog as a fruitful space for recursive and reflexive engagement from which may emerge concepts to further both mathematics and disability education. The opening question, "How can I know what's possible in terms of engaging students with disabilities in mathematical thinking and reasoning?," sparks discussion. Critique of typical practices in special education and mathematics teaching are raised in terms of learning theories and ideologies of schooling. Takeaways include the promise of emphasizing mathematical thinking as a way to structure more inclusive educational experiences for students with disabilities.