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The Supreme Court’s decision in Mayo Foundation for Medical Education and Research v. United States underscored the importance of a uniform approach to judicial review of administrative action; accordingly, the Court clarified that tax administration is generally subject to the same review as other kinds of administrative action by other federal agencies. Tax guidance from the IRS and Treasury Department serves an important role in clarifying the tax law so that taxpayers may report their tax liability accurately and plan their affairs. Meanwhile, aggressive attempts by a relatively small number of taxpayers to avoid tax liability by exploiting arguable ambiguities in the tax law present a perennial challenge for tax administration. In either case, as long as statutory and regulatory ambiguities exist, some surprises in the form of retroactive resolutions of uncertain tax positions are inevitable; the issue is who decides? Because of the Internal Revenue Code’s unusual grant of retroactive rulemaking power to the Treasury Department, tax administration cannot simply be collapsed with all other administrative action into a uniform framework of judicial review. This Article attempts to shed light on judicial review of more typical prospective tax guidance in part by drawing from the special case of retroactive tax guidance. This Article also argues that the general approach to judicial review of administrative action, as infused by the Code’s express grants of retroactive rulemaking power, affords the IRS and Treasury flexibility to make policy retroactively through rulemaking and receive deference from the courts. Moreover, though some constitutional limitations on retroactivity exist, the retroactive administrative clarification of an ambiguity should not be unconstitutional. Finally, this Article briefly assesses strengths and weaknesses of the current regime and the principal alternatives.