In visual question answering (VQA), a machine must answer a question given an associated image. Recently, accessibility researchers have explored whether VQA can be deployed in a real-world setting where users with visual impairments learn about their environment by capturing their visual surroundings and asking questions. However, most of the existing benchmarking datasets for VQA focus on machine “understanding” and it remains unclear how progress on those datasets corresponds to improvements in this real-world use case. We aim to answer this question by evaluating discrepancies between machine “understanding” datasets (VQA-v2) and accessibility datasets (VizWiz) by evaluating a variety of VQA models. Based on our findings, we discuss opportunities and challenges in VQA for accessibility and suggest directions for future work.