In this chapter, we survey some of the key tax issues that have confronted individuals operating in the sharing economy. While our discussion focuses on the United States, these classification, documentation, and compliance challenges frequently arise in other countries. Many of the tax implications of this work stem from the threshold decision by many platforms to classify such individuals as independent contractors rather than employees. Therefore, we first discuss how the threshold classification decision affects the substantive and compliance- related tax issues faced by individuals operating in the sharing economy. We briefly summarize the doctrinal tax rules governing income taxation of sharing economy workers, discussing both the rul...