This article draws from situated learning theory, teacher education research, and the authors' collaborative self-study to propose a teacher education pedagogy that may help to bridge the theory-into-practice gap for preservice teachers. First, we review the Interstate Teacher Assessment and Support Consortium standards to confirm the call for higher-order critical thinking skills as an essential habit for future classroom teachers. We also review literature of teacher education methodology and situated learning. Our self-study concerns the use of authentic role-playing as situated learning (ARSL), a situated learning methodology that allows our preservice teachers to pause the interaction during classroom role-playing in order to gain access to and demystify the complex, critical thinking used by expert teachers in their moment-to-moment practice. We describe two instances of ARSL in which we engaged preservice teachers in a fifth-grade mathematics lesson using tiered instruction. Implications for teacher education are discussed as we explore and analyze the problems we encountered in our attempts to improve our teacher education practices. (Contains 1 figure.)