The relationship between composition courses and online education is complicated, and attempting to summarize that relationship in a blanket statement may be feeble or futile. As a field, composition faces the challenge of identifying best practices in online education at the same time that it struggles to identify standardized content for its courses. Assessment challenges also plague online composition courses. While other fields might assess student work with standardized methods or computerized scoring, the work of composition requires tedious and labor-intensive assessment methods difficult to delegate to software; indeed, a recent petition illustrates significant instructor opposition to computer scoring (Haswell & Wilson, 2013). This chapter illustrates the current state of challenging conversations within composition studies as a kaleidoscope of positions in which instructors using online education position themselves.