Digital simulations offer learning opportunities to engage and reflect on systemic issues of racism and structural violence against communities of color. This talk examines how natural language processing tools can be used to better understand participants’ experiences within simulated environments focused on anti-racist teaching and identify changes in participants’ behavior over time. As K-12 schools increasingly reckon with our country’s long history of racist teaching practices, digital simulations may provide ways to help teachers name, re-examine, and reflect on their own practice and move toward anti-racist teaching. Dr. Joshua Littenberg-Tobias is a Research Scientist in the MIT Teaching Systems Lab. His research focuses on measuring and supporting learning within large-scale technology-mediated environments with a focus on civic engagement and anti-racist teaching practices. He received his Ph.D. from Boston College in 2015 in educational research, measurement, and evaluation.