Humans are evaluative by nature. It is quite likely one of the essential characteristics of our species that has allowed us to persist for hundreds of thousands of years. Despite what might be considered our almost instinctual inclination to assess or evaluate, we do not always do it well. There are any number of examples of the wrong questions being asked, or the wrong data being collected, or the wrong analysis being conducted, or the wrong conclusions being drawn. An aphorism, perhaps especially well known to readers of this text, warns, “Don’t judge a book by its cover.” The maxim concerns assumptions about almost anything except books. It carries with it the notion that features other than surface ones need to be taken into account when making decisions about something—or someone. This chapter addresses how to evaluate and assess online learning in particular and how to do so in a way that is systemic and systematic. This chapter is not about how to measure student learning within an online course, as that is a separate topic entirely; however, any evaluation of online learning may well include data on student progress.