Finding ways to make school math instruction more effective and relevant is important for supporting student pathways in STEM (Science, Technology, Engineering, and Mathematics). Mathematical tasks that describe real life situations represent an area of struggle for many K-12 students. This project uses a novel approach where free, high-quality illustrative diagrams are automatically generated for math problems using recent advances in generative AI. Illustrative diagrams are images that are visually compelling and artistic, while also containing mathematical information such as accurate measurements of geometric figures or the precise number of objects in a collection. Such images have typically been costly and time-consuming to produce; however, in this project, they will be created in a free and scalable way using cutting-edge AI approaches. The research will involve interviewing math teachers and Open Educational Resource developers (who produce free curriculum materials) about their needs and piloting methods for developing AI-enhanced illustrative diagrams in collaboration with these stakeholders. An experiment will then be conducted using the ASSISTments online homework platform to examine the effect of AI-generated illustrative diagrams on middle school students' mathematical learning. Using effective math visuals during instruction is an important way to impact students' interest and performance. The technical approach used in this project involves ControlNets,