Since the passage of the Tax Cuts and Jobs Act (TCJA) in 2017, the promulgation of regulations amplifying TCJA provisions has led practitioners to shift their attention to potential challenges to the Treasury Department’s (Treasury) interpretation of certain statutes. In this article, Tax Members George Hani and Loren Ponds examine a recently filed district court case, Liberty Global, Inc. v. United States, which raises novel arguments in asserting that the Treasury erred when it promulgated the temporary section 245A regulations. While the case is in its procedural infancy, it raises important issues that are likely to become recurring themes as we begin to see more audit cycles examining TCJA-enacted provisions. The authors conclude by noting that “with myriad open questions raised by the TCJA, even after the voluminous regulations issued by the Internal Revenue Service (IRS) and Treasury, audits of post-TCJA years are likely to include numerous disputed issues. Taxpayers would be well advised to take advantage of every tool that they can.” Liberty Global is a case worth watching to see how the court reacts to the taxpayer’s arguments and the government’s responses.