Loper Bright Archives | TAX CONTROVERSY 360

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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3M Co. v. Commissioner: IRS shipwrecks hard on the shoals of Loper Bright

by Edward L. Froelich | Oct 16, 2025 | Appellate Courts, Court Procedure Matters, Transfer Pricing Resource

3M Co. v. Commissioner, 136 AFTR 2d 2025-, (8th Cir.) (Oct.1, 2025), is perhaps the most significant tax case to date that implements Loper Bright’s instruction regarding evaluation of an agency’s exercise of delegated authority.[1] The unanimous panel held that:

The Internal Revenue Services’ (IRS) adjustment imputing additional royalty income to 3M from its Brazilian affiliate was invalid because it was outside the authority delegated by Internal Revenue Code Section 482.
The underlying regulation, Reg. § 1.482-1(h)(2) (the blocked income regulation), was invalid for the same reason.

The IRS’s change of tack

Those following the US Court of Appeals for the Eighth Circuit’s consideration of the case were aware that the Court had asked the parties to file supplemental briefing on the impact of the Loper Bright decision, which was handed down after the US Tax Court’s decision. The focus of the Tax Court dispute was whether the blocked income regulation was a valid implementation of the statute under Chevron and the Administrative Procedure Act. A plurality of that court agreed it was.

In its briefing before the Eighth Circuit, the IRS pivoted[2] and argued that even if the Court determined that the blocked income regulation was invalid, Code Section 482 provided direct authority to the IRS to make adjustments to income. The IRS maintained that it did not need a regulation to support the adjustment in the case. Moreover, the IRS argued, where adjustments relate to the transfer of intangible property (such as here), its authority was only constrained by the requirement that the adjustment conform to the income commensurate with that attributable to the intangible.[3] Because the parties agreed that the higher royalty would have been paid to an unrelated party, slip op. at 2, the IRS maintained it was authorized to make the adjustment to 3M’s income.

No one can be taxed on income they can’t have

The IRS’s maneuver did not deter the Eighth Circuit from carefully following the mandate it had received via Loper Bright to evaluate whether the agency’s exercise of authority was within its statutory mandate. In other words, even if the IRS could act without a regulation to make adjustments under Code Section 482, the exercise of its authority under that section must remain within the confines of the statute: “[I]t is still our job to ‘fix[] the boundaries of [that] delegated authority’ based on the statute’s text, as we have done today.” Slip. op. at 11 (quoting Loper Bright). Viewed through this lens, the Eighth Circuit found that the adjustments asserted by the IRS were well outside the authority granted by Code Section 482. Because the blocked income regulation purported to exercise the same extra-statute authority, it too was found deficient.

According to the Eighth Circuit, Code Section 482’s broad delegation to the IRS by its terms is limited to making adjustments where necessary to avoid evasion or distortion of income. However, in Comm’r v. First Sec. Bank of Utah, N.A., 405 U.S. [...]

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FedEx Defeats Government’s Loper Bright Gambit

by Samuel F. Hamer, Edward L. Froelich, Michael J. Scarduzio and Evan Walters | Mar 13, 2025 | Court Procedure Matters, IRS Guidance, Tax Refunds

On February 13, 2025, a Tennessee federal district court handed FedEx Corporation its second win in a refund action involving the application of foreign tax credits to what are known as “offset earnings.”[1] Offset earnings are earnings from a taxpayer’s profitable related foreign corporations that are offset by losses from other related foreign corporations. FedEx previously prevailed on the question of whether it was entitled to foreign tax credits related to such earnings.[2] In this most recent ruling, the court rejected the Government’s reliance on a certain regulatory provision called the “Regulatory Haircut Rule”[3] to argue that the amount of FedEx’s claimed refund should be reduced. The case now appears to be set for appeal.

Revisiting the analysis in its first ruling, the court explained the error of the Government’s reliance upon the Regulatory Haircut Rule. In short, the court said that the rule’s application conflicted with the best construction of the governing statutes, primarily Internal Revenue Code (IRC) Sections 960, 965(b)(4), and 965(g). The Government defended its reliance by appealing to Loper Bright’s instruction that courts must respect legitimate delegations of authority to an agency.[4] Citing IRC Section 965(o), which authorized the Secretary of the Treasury to prescribe regulations “as may be necessary or appropriate to carry out the provisions of” Section 965 and to “prevent the avoidance of the purposes” of this section, the Government argued that the Regulatory Haircut Rule furthered the IRC’s broader goal of preventing tax avoidance and that Loper Bright required the court to respect the Secretary’s exercise of his delegated authority.

While acknowledging that legitimate delegations of authority to agencies remain permissible after Loper Bright, the court reminded the Government that an agency does not have the power to regulate in a manner that is inconsistent with the statute, even when a delegation provision grants the agency broad discretionary authority:

Assuming that Congress delegated authority . . . to promulgate regulations implementing section 965 . . . that authority cannot, under Loper Bright, encompass the discretion to promulgate regulations that contravene the “single, best meaning” of section 965, as determined by the courts.[5]

In other words, a statute’s delegation provision should not be interpreted to allow Treasury to eliminate rules that Congress established in other parts of the IRC.

Practice Point: Referencing Loper Bright’s acknowledgment that Congress may “confer discretionary authority on agencies,”[6] the Government has defended (and likely will continue to defend) its regulations on the theory that its exercises of such authority should be respected. But as Loper Bright reminds us, courts have an independent duty to decide the meaning of statutory delegations. Thus, taxpayers should closely examine whether regulations purportedly derived from a statute’s delegation provision comport with the rest of the statute. Those that do not should be challenged.

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[1] FedEx Corp. & Subs. v. United States, No. 2:20-cv-02794 (W.D. Tenn., Feb. 13, 2025)(electronically available here).

[2] FedEx Corp. [...]

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