Since the advent of the Internet and the subsequent proliferation of online game worlds, millions of people across the physical world have spent vast amounts of time, money, and energy on virtual realms and their virtual lives. Taxation of transactions involving virtual goods may have been laughable at the outset of virtual reality, but the idea now bears serious consideration due to the growth of online video games into a multi-billion dollar industry. The IRS began efforts to address taxation of virtual economies in 2007, culminating in minor steps to effect compliance and a report by the Government Accountability Office released in May of 2013. This Article contends that the IRS is losing valuable tax revenue from sales of virtual goods for real money due to a lack of effective guidance in traversing this new frontier. And so, this Article establishes a spectrum of gamer profiles (social, vocational, casual, casual-hardcore, and hardcore) and uses that framework to craft tax compliance strategies in each virtual economy archetype. In addition, the Article provides brief overviews of popular multiplayer online games in the last decade (World of Warcraft, Second Life, League of Legends, etc.) and discusses the tax consequences of the most prevalent transactions relating to those virtual economies. It goes on to analyze the potential impact of current international taxation discourse on such transactions. The virtual universe and electronic commerce will only grow—and where income exists, taxation should follow.