Assessing the accessibility of online educational environments is not easy. As we scale up educational technology, like with Massive Open Online Courses (MOOCs), we may amplify the impact of (in)accessible designs. With MOOCs, we reach more learners and need to consider the variability that comes with scale. While the challenges and opportunities online learning at scale faces in terms of accessibility are great, the support from educators and technical experts of the platforms that host such courses has historically been minimal. In order to investigate the current state of accessibility in online educational environments, such as MOOCs, Chapter 15 reports on the development of a learning design evaluation checklist where Universal Design for Learning (UDL) has been adapted. After adapting design guidelines to an evaluation checklist, inter-rater reliability agreement protocols were used to improve and validate the checklist where two raters achieved a Cohen’s Kappa that ranged between 0.55 and 0.59 for three courses. This chapter details the reflective process followed to update the UDL framework, designed for developing accessible educational resources, to an evaluation checklist for MOOCs and the implications this process has for creating expert learners who are expert evaluators.