Economic Substance Doctrine
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IRS roundup: April 20 – May 1, 2026

Check out our summary of significant Internal Revenue Service (IRS) guidance and relevant tax matters for April 20, 2026 – May 1, 2026.

April 23, 2026: The IRS has reportedly begun the process of terminating a lead criminal investigation agent involved in probes of Malta pension structures and Puerto Rico’s Act 60 tax incentives, raising concerns about the continuity of those enforcement efforts. The agent was actively pursuing complex cases involving wealthy taxpayers and multinational structures, and his removal comes amid broader IRS workforce reductions and enforcement resource constraints.

The development has prompted questions from practitioners and policymakers about whether enforcement momentum in these areas will slow, even as the IRS continues to signal that investigations into offshore pension arrangements and Puerto Rico tax planning strategies remain ongoing.

April 24, 2026: The IRS Office of Chief Counsel issued Chief Counsel Advice 202617012, addressing when small corporations may qualify for a more liberal application of reasonable cause relief from penalties under § 6038A for failure to file Form 5472. The guidance explains that corporations with gross receipts of $20 million or less may be eligible if they meet specific criteria, including a lack of knowledge of the filing requirements, limited US presence, and prompt compliance once notified by the IRS.

The Office of Chief Counsel clarified that a “liberal” standard means the IRS should apply greater flexibility in evaluating reasonable cause, but taxpayers must still demonstrate good faith and reasonable cause to the satisfaction of the secretary.

April 29, 2026: The IRS published a notice announcing a public hearing on proposed regulations under § 45Z (the Clean Fuel Production Credit). The hearing has been expanded to run May 27 – 29, 2026, beginning at 9:00 am EDT each day. The proposed regulations address credit eligibility, life cycle emissions rates, and certification and registration requirements for clean fuel producers. Individuals seeking to attend the hearing must request access by May 22, 2026.

The IRS also released its weekly list of written determinations (e.g., Private Letter Rulings, Technical Advice Memorandums, and Chief Counsel Advice)

Recent court decisions

April 21, 2026: In Liberty Global, Inc. v. United States, in a split decision, the US Court of Appeals for the Tenth Circuit held that the codified economic substance doctrine under § 7701(o) applied to a taxpayer’s multistep transaction. The Court found that the taxpayer’s transaction structure generated no meaningful economic change and had no substantial non-tax purpose.

April 22, 2026: In Simmons v. Commissioner, T.C. Memo. 2026-34, the US Tax Court sustained the IRS’s deficiency determinations and accuracy-related penalties under § 6662(a), holding that the taxpayer failed to adequately substantiate several business and rental deductions. The Court found that the taxpayer did not meet the strict substantiation requirements of § 274(d) for automobile expenses and provided no evidence supporting claimed food expenses while also disallowing interest deductions under § 163(a) because the taxpayer failed to show that the expenses [...]

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Federal District Court Rules Codified Economic Substance Doctrine Vitiates Tax Transaction Benefits

On October 31, 2023, the US District Court for the District of Colorado, in Liberty Global, Inc. v. United States, applied the codified economic substance doctrine and held—on summary judgment—that Liberty Global, Inc. (LGI) must recognize $2.4 billion in taxable gain. At issue was a four-step transaction that took place in 2018, as a result of which LGI took the position that a dividends received deduction offset a $2.4 billion taxable gain based on a purported “mismatch” between (1) the rules for taxation of global intangible low-taxed income (GILTI) or subpart F income of a controlled foreign corporation (CFC) and (2) the qualification of an entity as a CFC.

In rejecting what it described as LGI’s “scheme” to “exploit” the apparent mismatch, the Court made three preliminary holdings. First, LGI argued that the prefatory clause in Internal Revenue Code (IRC) section 7701(o)—“[i]n the case of any transaction to which the economic substance doctrine is relevant”—requires courts to conduct a threshold analysis into whether the economic substance doctrine is “relevant” to the transaction at issue, and only then can courts consider whether the transaction has “economic substance.” The Court rejected this argument, stating that “there is no threshold ‘relevance’ inquiry that precedes the inquiry” into a transaction’s economic substance. Instead, “the doctrine’s relevance is coextensive with the statute’s test for economic substance.” Second, the Court held that the proper unit of analysis is “the transaction in aggregate” and did not analyze any step or phase in isolation, even if it could be said that the tax benefit at issue was “created” because of a particular step. And third, the Court denied LGI’s contention that its transaction falls under any exception to the economic substance doctrine. The Court determined that LGI’s transaction was not a “basic business transaction” and, although a series of transactions that constitute a corporate organization or reorganization might fall outside the economic substance doctrine, a series of transactions that merely includes a reorganization is not necessarily exempt.

The Court then applied the economic substance doctrine. LGI conceded that steps one through three “did not change, in a meaningful way, LGI’s economic position,” so the Court considered whether the steps had a substantial, non-tax purpose. LGI asserted that the transaction was “in furtherance” of Belgian corporate law requirements, but the Court found LGI had failed to indicate how the transaction facilitated such compliance. Moreover, an action may be “in furtherance” of some end without being a “substantial purpose” of the action, as IRC Section 7701(o) requires. Even if an isolated step provided substantial, non-tax benefits for LGI, that does not suggest the existence of a non-tax purpose for “the entire scheme.” Thus, the Court held that “the only substantial purpose of the transaction was tax evasion.”

The Court concluded that steps one through three of the transaction must be disregarded under federal law, resulting in $2.4 billion of taxable gain on LGI’s sale of its subsidiary during step four without such gain being converted to a dividend and [...]

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Update on IRS Enforcement Efforts

We frequently post about the Internal Revenue Service’s (IRS) tax enforcement trends and announcements. Prior examples from this year include the release of a five-year strategic plan emphasizing enforcement, the plan to hire up to 200 additional attorneys to assist with litigation efforts, the implementation of the Large Partnership Compliance (LPC) Pilot Program, a focus on tax compliance of non-US citizens and residents, and the creation of a new Joint Strategic Emerging Issues Team to identify emerging “abusive transactions.” Over the past several weeks, the IRS has provided additional updates on its enforcement efforts and future plans, including the following:

  • The IRS is considering raising the economic substance doctrine more frequently in transfer pricing examinations—even those where taxpayers have transfer pricing documentation—and asserting penalties more often in transfer pricing cases. This follows the announcement last April that executive approval is no longer needed before asserting the codified economic substance doctrine under Internal Revenue Code Section 7701(o).
  • The IRS plans to grow the LPC program and envisions it functioning similar to corporate examinations conducted by the Large Business & International Division.
  • The IRS’s Criminal Investigation (CI) Division is highly focused on criminal digital asset cases and intends to make many of these cases public. This follows the recent release of the CI Division’s annual report.
  • The IRS intends to expend more resources on examinations of high-income/high-net-worth taxpayers.
  • The IRS has proposed to require the disclosure of more information regarding corporate taxpayers’ uncertain tax positions, including citations to contrary authorities, which, if finalized, will likely lead to more examinations and challenges to tax reporting positions.

Practice Point: Tax enforcement has been down over the past several years, including a slowdown in audit operations during the COVID-19 pandemic. With increased funding from the Inflation Reduction Act of 2022 and proposed restrictions on access to IRS Appeals for certain matters, we expect more examinations and tax disputes in the near future. Taxpayers and their advisors should prepare. Consider working with your tax controversy advisor to discuss your more vulnerable return positions to see how to better defend against the impending tax enforcement wave!




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Santander Holdings USA Asks the Supreme Court to Address Economic Substance Doctrine

From 2003 to 2007, Sovereign Bancorp, Inc. (Sovereign) – now known as Santander Holdings USA, Inc. (Santander) – engaged in a so-called STARS transaction with Barclays Bank. According to Santander, “[b]y engaging in the STARS transaction, Sovereign transferred some of its income tax liability from the United States to the United Kingdom,” it “secured a loan of $1.15 billion,” and it received a payment “which effectively reduced its lending costs.” On its Federal corporate income tax returns for those years, Sovereign claimed foreign tax credits (FTCs) for UK taxes it paid in connection with the STARS transaction. It also claimed deductions for the interest paid on the $1.15 billion loan.

In 2009, the Internal Revenue Service (IRS) issued a Notice of Deficiency disallowing Sovereign’s FTCs and its deductions for interest paid on the $1.15 billion loan. The IRS did not challenge Sovereign’s compliance with the statutory and regulatory rules governing FTCs, instead arguing that Sovereign’s STARS transaction lacked “economic substance.” Sovereign paid the deficiency and sued for a refund in the US District Court for the District of Massachusetts. When the district court held for Sovereign on both issues, the IRS appealed to the US Court of Appeals for the First Circuit, but only with respect to the FTC issue. The crux of the issue was how to treat the UK taxes and the related FTCs for purposes of the “economic substance” analysis. Relying on Salem Financial, Inc. v. U.S., 786 F.3d 932 (Fed. Cir. 2015), and Bank of New York Mellon Corp. v. Comm’r, 801 F.3d 104 (2d Cir. 2015), the IRS argued that the UK taxes should be treated as an expense but that the related FTCs should be ignored in determining pre-tax profit. Citing IES Indus., Inc. v. U.S., 253 F.3d 350 (8th Cir. 2001), and Compaq Computer Corp. v. Comm’r, 277 F.3d 778 (5th Cir. 2001), Sovereign argued that either both should be included in the profit analysis or both should be ignored. The First Circuit held that Sovereign’s STARS transaction lacked “economic substance,” and upheld the disallowance of the FTCs at issue. In doing so, it treated the UK taxes as expenses that reduced pre-tax profit and ignored the related FTCs, following the Federal and Second Circuit’s approach. Santander Holdings USA, Inc. v. U.S., 844 F.3d 15 (1st Cir. 2016).

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