Abstract: Digital currency comes in many forms however Bitcoin stands out as the most popular. Bitcoin, released to the public in 2009, remains in the infancy stage of the technology lifecycle. Bitcoin has no regulatory body, central bank or government backing creating doubt as to the digital currency’s legitimacy. Despite Bitcoin’s lack of “official” recognition, the digital currency’s popularity continues to grow as the number of merchants and vendors accepting the currency expands globally. Focusing solely on the U.S. economy and monetary system, the lack of regulation and government recognition leaves legal disputes involving users of Bitcoin in the hands of a U.S. judicial system lacking previous case law as guidance. This research paper provides an in-depth analysis of the technical, economic and regulatory challenges facing the U.S. Federal Court system involving Bitcoin. A qualitative content analysis was employed in the exploratory review of 50 federal judicial cases involving Bitcoin. Key findings include discrepancies between the U.S. Judicial System and the U.S. Internal Revenue System on what and how to categorize Bitcoin, the value of bitcoin mining equipment, and the types of federal cases coming before the U.S. Judicial Courts involving Bitcoin.