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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 rules for income inclusion and the rules for expense tracking and taking. We then discuss some of the compliance challenges experienced by sharing economy participants in fulfilling their tax obligations, including the need to allocate expenses between business and personal use, the need to fi le estimated taxes, liability for self- employment taxes, and the need to track income given imperfect information reporting. The chapter then examines tax- related factors (such as lack of withholding) that may affect the labor- supply decisions of sharing economy participants. For example, we examine the potential impacts of lack of withholding and of expense estimation difficulties on how these individuals calculate their likely profit or loss from engaging in such work. Finally, we discuss possible reforms to the taxation of sharing economy participation that may help alleviate compliance challenges associated with work in this sector or may help these individuals make more informed decisions, and we explore the downsides of such reforms.