This paper discusses the challenges facing the IRS as it seeks to enforce taxpayer compliance regarding cryptocurrency transactions. For a proper analysis of these issues, we must look from the perspective of economic policy, as well as tax policy, including both domestic and global. The first part of addressing non-compliance is to abandon the idea that cryptocurrency is a currency. Instead, this paper will use “cryptoassets” to describe all types of digital and virtual currency. This broader term allows us to think beyond contemporary perspective and policy pertaining to cryptoassets and blockchain technology. Through that, the analysis will compare cryptoassets to other investments and securities, discuss the high potential for crime and fraud, examine the IRS’s current characterization of cryptoassets as property, and explore how other nations are implementing their own regulatory and tax policies for cryptoassets. Finally, this paper argues that to successfully enhance taxpayer compliance with taxable cryptoasset events in the United States, there needs to be a dual regulatory and policy shift, which can be accomplished on two fronts. First, by creating a regulatory foundation that incentivizes taxpayers to comply with tax law. And second, by carving out a special tax characterization for cryptoassets and taxable transactions related to cryptoassets.