This week, Sloan Speck (Colorado) reviews a new work by Benjamin Silver, The Tax Insurance Trap, 2026 Wis. L. Rev. __ (forthcoming).

Since the early 2000s, the tax insurance industry has boomed. Today, tax insurance is commonplace, covering risks from tax status violations to adverse transactional treatment with policy limits into the billions. In a compelling new article, Benjamin Silver offers fresh perspectives—positive and normative—on this maturing industry. Silver juxtaposes tax insurance with the tax Anti-Injunction Act (TAIA), which generally bars taxpayers’ legal claims prior to assessment or collection. Taxpayers must leap before they can use courts to look into the applicable tax law. From this perspective, tax insurance operates as a “synthetic pre-enforcement challenge” that eliminates ex ante uncertainty associated with a specific tax position—a private-sector solution to the TAIA’s strictures (6). Silver’s novel framing rationalizes the policy role of tax insurance and sheds new light on how these products should be treated.

After developing this analytic framework, Silver rejects tighter regulation of the tax insurance industry and recommends clarifying tax insurance’s federal income tax treatment. Under Silver’s prescriptions, premiums for tax insurance would be deductible, and the proceeds, if any, of such policies would be excludible—a double tax benefit. (Silver might clarify whether these benefits also apply to policies written for state or non-income tax liabilities.) Although Silver frames this tax treatment as comparable to pre-enforcement challenges outside of tax law (54), the tax benefits that Silver would attach to both parts of tax insurance policies—premiums and payouts—may represent a subsidy akin to that afforded by Congress to employer-provided health insurance. Economists and legal academics, of course, have long excoriated the double benefit for employees’ health insurance as distortionary and distributionally malign. My sense is that, in the context of tax insurance, the question is whether lawmakers should subsidize purchases of the product, and, if so, what this subsidy’s effects would be.

Silver imposes two guardrails on his deductible-not includible schema: this doubly favorable tax treatment would not attach to policies providing either general tax insurance or insurance for tax shelters or reportable transactions (56). There are real teeth in these restrictions. However defined, the “tax shelter” restriction has in terrorem effects that may cabin tax insurance to genuine transactions or legal arrangements. Moreover, Silver’s exclusion of loss transactions and transactions of interest from favorable tax treatment discourages deals in these potentially pernicious categories. And Treasury’s discretion in identifying transactions of interest gives a means for indirect oversight of the tax insurance market. The result might be analogous to life insurance, where double benefits accrue to employer-provided policies with payouts up to $50,000, while other life insurance policies receive only a single tax benefit on payout. Although others might delineate the preferred and nonpreferred categories of tax insurance differently, my intuition is that segmentation of this sector is correct from a policy perspective. Some types of tax insurance eliminate tax frictions with respect to beneficial private activity, while others may encourage inappropriate tax risks. The trick, as Silver indicates, is finding the right balance.

Finding this balance is hard, in part, because premiums for tax insurance incorporate multiple risks with different social costs. Premiums principally reflect the potential for adverse ex post outcomes under uncertain tax law—an insurable risk that Silver rightly views as a barrier to otherwise efficient arrangements. But, as Heather Field and Kyle Logue have emphasized, tax insurance premiums also reflect audit risk and detection risk. For a policy to pay out, the IRS must first audit the taxpayer, then detect the relevant uncertainty under tax law, then resolve that uncertainty against the taxpayer. Litigation may ensue. The probability of step one is low, and likely declining. The same with step two, given the inherent difficulty in reading transactions retrospectively, rather than as they are constructed. These two procedural gates push down tax insurance premiums to something far less than the expected costs of an adverse outcome under tax law, applied full-bore. Any policy prescriptions for tax insurance should account for the “audit lottery,” probably through less-favorable treatment for at least some subset of tax insurance policies.

Finally, Silver’s framing and arguments draw into question whether policymakers should revisit tax law’s other mechanisms that implicate pre-enforcement review. For example, Congress might loosen or repeal the TAIA and allow up-front judicial review of some or all tax laws. Silver sees such a change as potentially benign, with “few pre-enforcement challenges” brought by taxpayers (23). My sense is that there’s a lot a stake in the types of claims that would be brought, absent the TAIA. Most notably, I would expect an increase in cause litigation and constitutional challenges. Whether these types of claims should be heard is a separate question but one worth engaging after the hash of ugly facts and legal claims that was Moore v. United States. Alternatively, Silver’s paper might serve as a call to revamp IRS’s private letter ruling processes to be more competitive with private-sector tax insurance. The ruling process could be streamlined or firewalled from audit teams. Although these issues are mostly outside of Silver’s project, I would expect them to arise organically as the tax insurance market becomes ubiquitous (and Silver’s recommendations clearly would push in this direction). Tax insurance is rebalancing the tax system’s public-private system of administration, and policymakers should approach these changes as an opportunity to rethink U.S. tax administration on a more fundamental level.

Overall, Silver’s article is an important and valuable contribution to the academic literature on tax insurance. By reframing tax insurance in terms of the TAIA, Silver elucidates original insights about how these products operate in tax law, and Silver’s article should be of significant interest for economists and legal scholars, as well as policymakers.

Here’s the rest of this week’s SSRN Tax Roundup:

Abdulmudallib Salihu Abubakar (Independent), Tax Law Rewrite and Simplification: A Critical Assessment of the Nigerian Tax Reform ACTS, 2025 (Aug. 30, 2025)

Christian Bauer (Vienna U. Econ. & Bus.), A Tax Audit Taxonomy: A Systematic Review of Operational Definitions and Behavioral Impacts, WU Int’l Tax’n Rsch. Paper Ser. No. 2025-09 (Nov. 5, 2025)

Sergio Carbone (Independent), Loss of Tax Residency: And the Importance of Completing the Procedures Before the National Tax Authority in Due Time and Proper Form (Oct. 13, 2025)

Shuping Chen (Texas, McCombs Sch. Bus.), Nicholas Hallman (Texas, Salem Ctr. Pol’y) & Albert Di Wang (Texas, McCombs Sch. Bus.), International PCAOB Inspections and the Decline in Foreign Listings to the United States (Nov. 3, 2025)

Akshita Choudhary (Gujarat Nat’l L. U.), Ishita Ghughariwala Ishita (Gujarat Nat’l L. U.) & Pankti Rupani (Gujarat Nat’l L. U.), Economic Substance Requirements Versus Tax Residency Certificates: A Comparative Analysis of Anti-Abuse Mechanisms in Developing Countries Post-BEPS (Oct. 1, 2025)

Conor Clarke (Wash. U.) & Ari Glogower (Northwestern), Tariffs and the Taxing Power: Historical Lessons for Major Questions and Nondelegation, 103 Wash. U. L. Rev. __ (forthcoming 2026)

Kenny Dekoster (Ghent U., Dept. Acct.), Isabelle Verleyen (Ghent U.), Annelies Roggeman  (Ghent U., Dept. Acct.) & Catherine Acosta Garcia (Ghent U.), CSR Communication to Manage Reputational Risks from Tax Aggressiveness Allegations: An Evaluation of Congruence and Timing (Oct. 24, 2025)

Mia Galgau (Nat’l Distance Educ. U.), Tax Havens Versus Tax Hells: Reconfiguring Global Fiscal Power in the 21st Century (Oct. 5, 2025)

David Gamage (Missouri) & Darien Shanske (UC Davis), NCTI is the New GILTI, and States Should Still Conform, 117 Tax Notes State 799 (Sept 22, 2025)

Mingze Gao (Macquarie U., Bus. Sch.), Thanh Son Luong (U. Sydney, Bus. Sch.), Buhui Qiu (U. Sydney, Fin.), Krishan Shankar (U. Sydney) & Eliza Wu (U. Sydney, Bus. Sch.), Corporate Tax Reform and the Cost of Bank Loans: Evidence from the Tax Cuts and Jobs Act (Nov. 12, 2025)

Svea Holtmann (U. Mannheim, Acct. & Tax’n), Anna-Sophie Braun (Catholic U. Eichstaett-Ingolstadt), Jae Cho (Ludwig Maximilian U. Munich, Dept. Econ.), Reinald Koch (Catholic U. Eichstaett-Ingolstadt) & Dominika Langenmayr (Catholic U. Eichstaett-Ingolstadt), Investment Effects of a Quasi-Robot Tax: Evidence from South Korea (Nov. 4, 2025)

Svea Holtmann (U. Mannheim, Acct. & Tax’n), Dominika Langenmayr (Catholic U. Eichstaett-Ingolstadt), Valeria Merlo (U. Tübingen) & Georg Wamser (U. Tübingen), Corporate Taxation and Firm Productivity (Nov. 5, 2025)

Yusuke Hoshiai (Mitsubishi Rsch. Inst.) & Shun-ichiro Bessho (Waseda U., Pol. Sci. & Econ.), Electronic Tax Filing, Compliance Costs and Tax Evasion: Evidence from Japanese Corporations (Nov. 8, 2025)

Assan Jallow (U. Wis. Whitewater, Coll. Bus. & Econ.), Dancing on Tax Waters: An Objective Analysis of Residents’ and Non-Residents’ Taxation in the Gambia (Oct. 11, 2025)

Miriam Kamper (U. Passau), The Mandatory Disclosure Rules—A Boost for Tax Transparency and Audit Accuracy? (Nov. 13, 2025)

Miriam Kamper (U. Passau) & Markus Diller (U. Passau), The Blurry Line Between Tax Avoidance and Tax Evasion—Theoretical Framework and Game Theoretic Impact (Nov. 7, 2025)

Pramod Kumar (Independent), Beneath the Surface: Beyond the Headlines Section 94B(1) Proviso—Myth vs. Reality (Oct. 12, 2025)

Rupert Macey-Dare (St. Cross Coll., U. Oxford), VAT on UK Private School Fees—Economics, Law & Politics (Oct. 7, 2025)

Michael Mayberry (U. Florida, Fisher Sch. Acct.), Marvin Nipper (Friedrich-Alexander-U. Erlangen-Nürnberg) & Marius Weiß (Friedrich-Alexander-U. Erlangen-Nürnberg), Personal Income Taxes and Corporate Pollution (Nov. 7, 2025)

Mika Nissinen (U. E. Finland), Christian Bauer (Vienna U. Econ. & Bus.), Moritz Scherleitner (Aalto U., Bus. L.), Hannu Ojala (U. E. Finland) & Erich Kirchler (U. Vienna, Psychology), The Right Tool at the Right Time—Perceived Fairness and Trust in the Stages of a Modern Tax Process, WU Int’l Tax’n Rsch. Paper Ser. No. 2025-13 (Nov. 5, 2025)

Tamir Shanan (Coll. Mgmt), The Domicile Principle in Israel’s Tax System, Hapraklit (Isr. Bar Assn.) L. Rev. (2025)

Tamir Shanan (Coll. Mgmt.) & Doron Narotzki (Akron, Accountancy), Regressive Aspects in the Taxation of Equity-Based Compensation for Employees, 11 Reg. Stud. 155 (2025)

Tamir Shanan (Coll. Mgmt.) & Doron Narotzki (Akron, Accountancy), Taxation of Decentralized Encrypted Virtual Payment Methods in Israel, 11 Reg. Stud. 245 (2025)

Alfred Söderberg (RISE Rsch. Inst. Swed.), Taxing Free Workplace Parking: Explaining Low Employer Compliance in Sweden (Nov. 6, 2025)

Michel Strawczynski (Hebrew U. Jerusalem, Pub. Pol’y), Cyclicality of Tax Expenditures (Nov. 5, 2025)

Alex Zhang (Emory), The Other Taxation: Tribes, Territories, and Fiscal Autonomy, 126 Colum. L. Rev. __ (forthcoming 2026)

Libin Zhang (Fried Frank), Marginal Tax Rates of the Individual Alternative Minimum Tax, 188 Tax Notes Fed. 811 (Aug. 4, 2025)