As environments continue to shift around teaching and learning, so do the measurements and the scale for assessment. Bill Gates has claimed that “the value of MOOCs comes when you use them to create hybrids that are the best of both worlds (Brahimi, 2011),” and herein lies an inherent problem in the nature of the MOOC courses: If MOOCs are uniquely poised to bring about transformative change between the world and the classroom as we know it, how are these new features around assessment being implemented and scaled for a growing audience with a unique set of individual needs? Large scale assessments, like those common to MOOCs, currently struggle to provide valid and reliable assessment for their many learners. In these massive online open courses the experts are typically outnumbered by the learners and the issue of fair and balanced assessment is a difficult, if not impossible goal. Ultimately a conflict between the digital and traditional classroom space urges the question: how can MOOCs and their assessments be scaled to provide “the best of both worlds?”