In real-world settings, vision language models (VLMs) should robustly handle naturalistic, noisy visual content as well as domain-specific language and concepts. For example, K-12 educators using digital learning platforms may need to examine and provide feedback across many images of students' math work. To assess the potential of VLMs to support educators in settings like this one, we introduce DrawEduMath, an English-language dataset of 2,030 images of students' handwritten responses to K-12 math problems. Teachers provided detailed annotations, including free-form descriptions of each image and 11,661 question-answer (QA) pairs. These annotations capture a wealth of pedagogical insights, ranging from students' problem-solving strategies to the composition of their drawings, diagrams, and writing. We evaluate VLMs on teachers' QA pairs, as well as 44,362 synthetic QA pairs derived from teachers' descriptions using language models (LMs). We show that even state-of-the-art VLMs leave much room for improvement on DrawEduMath questions. We also find that synthetic QAs, though imperfect, can yield similar model rankings as teacher-written QAs. We release DrawEduMath to support the evaluation of VLMs' abilities to reason mathematically over images gathered with educational contexts in mind.