This Article queries how the administrative tax guidance used to implement the Tax Cuts and Jobs Act of 2017 has met the normative commitment to democratic legitimacy that often animates general administrative law. This Article argues that several reforms to the tax administrative process that came to fruition in recent years have failed to advance democratic tax administration. This argument is made by analyzing each piece of administrative guidance issued to implement the Tax Cuts and Jobs Act, as compared to similar guidance issued to implement tax cuts in 2001, as well as the Tax Reform Act of 1986. To do this, we created a database of 864 guidance documents issued across six total years in three time periods: 1986–1988, 2001–2003, and 2017–2019. Our examination shows that although tax procedures may now better conform to procedures applied by other administrative agencies, these changes have in some respects set back the pursuit of democratic legitimacy in tax administration. The changing practices identified here have important implications for democratic engagement and accountability in tax administration. For example, this Article critiques a specific change that our study reveals has had stark effects—tax administrators have almost totally abstained from using so-called temporary regulations. While this move has been promoted by scholars specifically as a way to address democratic legitimacy concerns related to transparency and participation in the tax rulemaking process, this Article argues on doctrinal and normative grounds that avoidance of temporary regulations is misplaced and should (and can) be reversed in part so as to better realize democratically legitimate tax administration.