Textbooks are the primary vehicle for delivering quality education to students. It has been shown that explanatory or illustrative visuals play a key role in the retention, comprehension and the general transfer of knowledge. However, many textbooks, especially in the developing world, are low quality and lack interesting visuals to support student learning. In this paper, we investigate the effectiveness of vision-language models to automatically enhance textbooks with images from the web. Specifically, we collect a dataset of e-textbooks from one of the largest free online publishers in the world. We rigorously analyse the dataset, and use the resulting analysis to motivate a task that involves retrieving and appropriately assigning web images to textbooks, which we frame as a novel optimization problem. Through a crowd-sourced evaluation, we verify that (1) while the original textbook images are rated higher, automatically assigned ones are not far behind, and (2) the choice of the optimization problem matters. We release the dataset of textbooks with an associated image bank to spur further research in this area.