TAX CONTROVERSY 360

Potential refund opportunity of buyback excise tax based on § 4501 final regulations

by Shawn O’Brien, Brian H. Jenn, Edward L. Froelich, Nick Ryan and Matthew J. Blaney | Dec 15, 2025 | IRS Guidance, Tax Refunds

Taxpayers who paid the stock repurchase excise tax based on prior guidance provided in Notice 2023-2 and the proposed regulations under Internal Revenue Code (IRC) § 4501 may be entitled to a refund based on changes made in the recently issued IRC § 4501 final regulations.

On November 21, 2025, the US Department of the Treasury (Treasury) and the Internal Revenue Service (IRS) issued final regulations under IRC § 4501, which took effect on November 24 and significantly narrowed the applicability of the stock repurchase excise tax compared to prior guidance provided in Notice 2023‑2 and the April 9, 2024, proposed regulations (collectively, the prior guidance). As a result, many transactions that were previously treated by the prior guidance as “repurchases” subject to the 1% stock repurchase excise tax are now no longer taxable. Taxpayers who paid the excise tax based on the prior guidance may be eligible for a refund.

The final regulations eliminated the prior guidance’s broad “funding rule,” which treated a US affiliate that was considered to have “funded” a foreign publicly traded parent (or its foreign affiliates), including via distributions or capital contributions, as having engaged in a covered stock repurchase. The final regulations also significantly narrowed the proposed regulations’ expansive treatment of transactions as “economically similar” to a stock repurchase by specifically excluding leveraged buyouts and other take-private transactions, complete liquidations, and tax-free acquisitive reorganizations under IRC § 368 from being subject to the excise tax. Moreover, the final regulations narrowed what qualifies as “stock” for IRC § 4501 purposes, specifically excluding certain preferred stock described in IRC § 1504(a)(4) (e.g., “plain vanilla” non-voting, non-participating preferred stock) and certain mandatorily redeemable or puttable stock issued before August 16, 2022 (i.e., the date of enactment of IRC § 4501).

The changes in the final regulations have potentially sweeping implications for taxpayers who paid the IRC § 4501 stock repurchase excise tax based on the prior guidance. The narrower scope of the applicability of stock repurchase excise tax under the final regulations creates a substantial opportunity to seek a refund of stock repurchase excise tax previously paid under the now-obsolete prior guidance.

To seek a refund, taxpayers should file Form 720-X, Amended Quarterly Federal Excise Tax Return, for each quarter they filed an original Form 720 reporting and paid the stock repurchase excise tax and attach a Form 7208 (with “Amended” at the top of each form) to each quarterly Form 720-X. Both Form 720-X and amended Form 7208 should be completed, and the excise tax recomputed, based on the final regulations. Because Form 720-X will serve as the taxpayer’s refund claim, it is critical that Form 720-X contains a detailed explanation of the legal basis for the adjustments to the original Forms 720 and 7208 to meet regulatory requirements imposed by the Treasury on refund claims. See Treas. Reg. § 301.6402-2 (setting forth the basic requirements for refund claims).

Taxpayers considering this refund opportunity should be aware that the statute of limitations deadline for filing a refund [...]

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Major update: Potential refund opportunity for interest and penalty amounts accrued during COVID-19 federally declared disaster

by Shawn O’Brien and Samuel F. Hamer | Dec 8, 2025 | Court Procedure Matters, IRS Appeals, IRS Audits, Penalties, Settlements, Significant Court Decision, Tax Refunds

The US Court of Federal Claims’ (CFC) recent decision in Kwong v. United States, No. 23-267 (Fed. Cl. Nov. 25, 2025), provides significant support for the potential refund opportunity we identified in a previous blog post titled, “Refund opportunity for interest and penalty amounts accrued during COVID-19 federally declared disaster.” The refund opportunity applies to taxpayers who made payments to the Internal Revenue Service (IRS) that included underpayment interest and/or failure-to-file/failure-to-pay penalties that accrued during all or part of the period from January 20, 2020, through July 10, 2023.

Although the CFC’s holding in Kwong addressed whether Internal Revenue Code (IRC) § 7508A provided the taxpayer an extension of the two-year statute of limitations deadline for filing a refund suit (in IRC § 6532(a)) that fell after the COVID-19 disaster was declared, Kwong answered important questions for those taxpayers pursuing refunds for underpayment interest and/or failure-to-file/failure-to-pay penalties that accrued during COVID-19. The CFC held that the 2019 version of IRC § 7508A applies to the COVID-19 federally declared disaster. This is a significant holding because Congress amended IRC § 7508A in 2021 to significantly limit the IRC § 7508A(d) mandatory extension period. The CFC also held that the IRC § 7508A(d) mandatory extension period, as applied to the COVID-19 disaster, commenced on January 20, 2020, and ended on July 10, 2023.

Kwong has potentially sweeping implications for taxpayers who faced federal tax filing and/or payment deadlines that fell between January 20, 2020, and July 10, 2023. Under the CFC’s Kwong analysis, the deadline for payment of any federal tax falling between these two dates was extended to July 11, 2023. Since the IRS computes underpayment interest and/or failure-to-file/pay penalties from the payment due date, penalties should not accrue from January 20, 2020, through July 10, 2023, and any taxpayers who already paid these amounts may be entitled to a refund. The CFC’s analysis also does not rule out the possibility that taxpayers with payment due dates preceding January 20, 2020, may be entitled to relief to the extent the underpayment interest and/or failure-to-file/failure-to-pay penalties accrued during the COVID-19 disaster period.

As noted in our previous post, taxpayers considering this refund opportunity should be aware that the statute of limitations to file a refund claim expires three years from the filing deadline of the original tax return or two years from the date on which payment was made, whichever is later (unless the statute of limitations period was otherwise extended). This refund opportunity may apply to underpayment interest and/or penalties paid with respect to federal income, estate, gift, employment, or excise taxes.

IRS roundup: November 7 – November 24, 2025

by Evan Walters, Samuel F. Hamer, Edward L. Froelich, Michael J. Scarduzio and Matthew J. Blaney | Dec 2, 2025 | Court Procedure Matters, IRS Guidance, Significant Court Decision, Tax Reform

Check out our summary of significant Internal Revenue Service (IRS) guidance and relevant tax matters for November 7, 2025 – November 24, 2025.

November 10, 2025: The IRS released Internal Revenue Bulletin No. 2025-46, which includes proposed regulations 109742-25. The proposed regulations would remove a rule in previous final regulations that uses the shareholders of certain domestic corporations to determine whether foreign persons hold – directly or indirectly – stock in a domestically controlled qualified investment entity (QIE). If a QIE was not domestically controlled following the changes from the proposed regulations, stock owned by foreign persons in a QIE would qualify as a US real property interest.

November 10, 2025: The IRS released Revenue Procedure 2025-31, providing guidance on a safe harbor that allows trusts qualifying as investment trusts under Section 301.7701-4(c) and as grantor trusts to stake digital assets without losing their tax status and offering a limited period for existing trusts to amend their governing instruments to meet the safe harbor requirements.

November 13, 2025: The IRS released Notice 2025-67, which announces the annual cost-of-living adjustments to the limits on benefits and contributions for qualified retirement plans under Section 415 of the Internal Revenue Code (Code). These adjustments, required by Section 415(d), follow procedures similar to those used for Social Security benefit updates and apply to certain amounts under deferred compensation plans.

November 13, 2025: The IRS released Revenue Ruling 2025-22, announcing that interest rates will remain unchanged for the calendar quarter beginning January 1, 2026. The rates are as follows:

7% for individual overpayments and 6% for corporate overpayments
5% on the portion of a corporate overpayment exceeding $10,000
7% for underpayments and 9% for large corporate underpayments

Under the Code, these rates are recalculated quarterly based on the federal short-term rate. For noncorporate taxpayers, both overpayment and underpayment rates equal the federal short-term rate plus three percentage points. For corporations, the underpayment rate is also the short-term rate plus three points while the overpayment rate is the short-term rate plus two points. Large corporate underpayments add five points, and corporate overpayments exceeding $10,000 add 0.5 points. The current rates are based on the federal short-term rate determined in October 2025.

November 19, 2025: The IRS announced that it would resume its regular activities following the 2025 lapse in appropriations during the government shutdown. In its announcement, the IRS included specific frequently asked questions regarding the resumption of regular activities for audits, collections, and appeals and stated that determination letter applications for tax exempt and government entities would resume.

Recent court decisions

November 5, 2025: The US District Court for the Northern District of Texas issued an opinion in Ryan, LLC v. IRS. Check out our recent insight on the case, including an analysis of the district court’s holdings and practice points for taxpayers.

November 12, 2025: The US [...]

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Tax consulting firm permitted to challenge final micro-captive reporting regulations

by Samuel F. Hamer | Dec 2, 2025 | Court Procedure Matters, Significant Court Decision, Trial Courts

Ryan, LLC v. Internal Revenue Service[1] is the latest example of success in overcoming procedural hurdles to challenge the validity of a US Department of the Treasury (Treasury) regulation. In a recent opinion, the US District Court for the Northern District of Texas held that:

Ryan has standing to challenge the validity of the Treasury’s final regulations[2] that require disclosure of certain transactions engaged in by businesses and their “micro-captive insurance companies” (MCICs).
Ryan sufficiently pleaded its claim that the final regulations under challenge were “arbitrary, capricious, an abuse of discretion, or otherwise not in accordance with law” and must be set aside under the Administrative Procedure Act (APA).[3]
The court’s opinion confirms that nontaxpayer actors may have standing to challenge Treasury regulations. The case is also another example of a plaintiff reaching the merits stage of a challenge to a Treasury regulation in the aftermath of Loper Bright v. Raimondo.[4]

Background

Ryan is an advisor to businesses seeking to establish and maintain MCICs. “Captive” insurance companies are specialized insurance companies that exist to insure the entities that own them. When the owning entities make premium payments to the captive, the premiums do not need to include commissions or other fees associated with traditional insurers, making captives an attractive option especially when coverage is unavailable or costly through traditional insurers. Certain small captive insurance companies, commonly called MCICs, qualify for favorable tax treatment. Under section 831(b), MCICs are not taxed on the first $2.2 million in premiums paid by their owner-insured. The Internal Revenue Service (IRS) has increased its scrutiny of the captive insurance industry because of concerns that these arrangements may be exploited for fraud and abuse.

The Treasury’s new regulations

Section 6707A requires the disclosure of certain “reportable transactions,” defined as transactions that, in the IRS’s determination, have a “potential for tax avoidance or evasion.” A “listed transaction” is a type of reportable transaction in which the taxpayer is presumed to have engaged in the transaction for the purpose of tax avoidance or evasion.[5] A “transaction of interest” is a reportable transaction designated by the IRS as having a potential for abuse but is not presumed abusive.[6] These designations create heavy reporting requirements by taxpayers and their advisors (e.g., Ryan).

Under the Treasury’s new regulations, a micro-captive insurance transaction is defined based on a loss ratio factor and a financing factor. The loss ratio factor is the ratio of the captive insurance company’s cumulative insured losses to the cumulative premiums earned over a specified period, typically the most recent 10 taxable years (or all years if less than 10). The financing factor refers to whether the captive insurance company participated in certain related-party financing arrangements within the most recent five taxable years, such as making loans or other transfers of funds to insureds, owners, or related parties. A transaction is classified as a “listed transaction” if the MCIC’s loss ratio is [...]

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Tax Court confirms codified economic substance doctrine requires threshold relevancy determination, upholds 40% strict-liability penalty

by Susan E. Ryba and Edward L. Froelich | Nov 24, 2025 | Court Procedure Matters, Significant Court Decision, Trial Courts

Patel v. Commissioner, 165 T.C. No. 10 (Nov. 12, 2025), gave the US Tax Court its “first opportunity to examine when the codified economic substance doctrine applies.” Patel at *16. The Tax Court made two key holdings:

Section 7701(o) requires a relevancy determination that “is not coextensive with the two-part test set forth in section 7701(o)(1)(A) and (B).” Patel at *17.

Adequate disclosure to reduce the 40% economic substance penalty imposed by sections 6662(b)(6) and (i) must be made at the time the return is filed and not at a later time. Patel at *30.

Relevancy determination

Section 7701(o) provides:

Sec. 7701(o). Clarification of economic substance doctrine.—

(1) Application of doctrine.—In the case of any transaction to which the economic substance doctrine is relevant, such transaction shall be treated as having economic substance only if—

(A) the transaction changes in a meaningful way (apart from Federal income tax effects) the taxpayer’s economic position, and

(B) the taxpayer has a substantial purpose (apart from Federal income tax effects) for entering into such transaction.

While the Internal Revenue Service (IRS) endorses a seemingly limitless application of the codified economic substance doctrine, taxpayers contend that it does not apply to every transaction. Rather, the plain language of section 7701(o)(1) requires a threshold relevancy determination. If the economic substance doctrine is not relevant, the inquiry ends.

There are very few cases that have considered whether section 7701(o) requires a threshold relevancy determination. And those that have found that section 7701(o) does not impose a separate relevancy requirement. See Liberty Global, Inc. v. United States, No. 20-cv-63501, 2023 WL 8062792 (D. Colo. Oct. 31, 2023); Chemoil Corp. v. United States, No. 19-cv-6314, 2023 WL 6257928 (S.D.N.Y. Sept. 26, 2023). While Liberty Global was appealed to the US Court of Appeals for the Tenth Circuit – and many speculate the Tenth Circuit may clarify that there is a relevancy requirement – the Tax Court beat the appellate court to the punch.

The Tax Court’s holding had solid statutory support. The plain language of section 7701(o)(1) states: “In the case of any transaction to which the economic substance doctrine is relevant…” After quoting these words, the Tax Court stated, “we easily conclude that the statute requires a relevancy determination. To put it plainly—the statute says so, right there, on its face.” Patel at *17.

Adequate disclosure of transactions

The second key holding in Patel is that the taxpayers in the case are liable for a 40% penalty for engaging in a transaction that lacks economic substance that was not adequately disclosed. Section 6662(b)(6) imposes a 20% penalty on transactions that lack economic substance. This penalty is increased to 40% under section 6662(i) if the transaction is not adequately disclosed.[1]

In the current wave of economic substance challenges, it is unclear what constitutes adequate disclosure under section 6662(i) such that the 20% (instead of the 40%) penalty applies. Based on current audit activity, [...]

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