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Recent Tax Developments Concerning Administrative Law Issues

We have written extensively on the intersection of tax law and administrative law, specifically on how the Administrative Procedure Act (APA) and the Anti-Injunction Act (AIA) factor into tax cases. In a recent article for the ABA Tax Times, Kristin E. Hickman, a leading authority in the fields of tax administration, administrative law and statutory interpretation, discusses several tax opinions from 2022 concerning APA issues. We think this article is a must-read for taxpayers and practitioners.

For some of our prior posts on tax law and administrative law, see below:




Courts Outline Boundaries of the Anti-Injunction Act Post-CIC Services

Since the Supreme Court of the United States’ decision in CIC Servs., LLC v. IRS was issued in May 2021, courts have grappled with how to apply the Anti-Injunction Act (AIA) in other contexts. The US Court of Appeals for the Eleventh Circuit recently affirmed the dismissal of a lawsuit under the AIA in Hancock County Land Acquisitions, LLC v. United States, while the Court of Appeals for the First Circuit recently held that the AIA does not prevent a challenge to the Internal Revenue Service’s (IRS) use of John Doe summons in Harper v. Rettig.

In July, we posted about a circuit split between the Sixth and Eleventh Circuits over claimed Administrative Procedure Act (APA) violations. As discussed below, these post-CIC Services decisions are shaping the boundaries of challenges based upon the APA and the AIA.

THE ELEVENTH CIRCUIT

The taxpayer in this case reported a $180 million deduction for a conservation easement on land it owned in Mississippi. The IRS audited the taxpayer and requested an extension of the statute of limitations on assessment in Internal Revenue Code (IRC) Section 6501. The taxpayer initially declined, but 11 months after the request it agreed to extend the limitations period. At that point, the IRS had almost finished with its examination, and the parties never executed the extension. The IRS issued a Notice of Final Partnership Administrative Adjustment (FPAA), and the taxpayer was unable to pursue an administrative resolution with the IRS Office of Independent Appeals (IRS Appeals). The taxpayer filed suit in US federal district court, arguing, among other things, that the IRS violated the APA when it did not send the case to IRS Appeals, resulting in the taxpayer being deprived of pre-litigation administrative resolution of its tax dispute. The IRS moved to dismiss the complaint for lack of subject matter jurisdiction, which the district court granted.

On appeal, the taxpayer argued that the suit was not barred by the AIA, citing CIC Services. The Eleventh Circuit, however, explained that the three considerations that led to that conclusion in CIC Services were the “same three considerations [that] lead to the opposite conclusion here.” The Court found that the taxpayer: (1) would not be subject to any costs separate and apart from the tax penalty from the FPAA; (2) was on the cusp of liability when it filed its suit and (3) would not suffer any criminal punishment by following the AIA’s “familiar pay-now-sue-later procedure.” The Court stated, “at its heart, this suit is a ‘dispute over taxes,’” and it was far from clear that under no circumstances could the IRS prevail on the merits of the taxpayer’s claim.

THE FIRST CIRCUIT

In 2013, the taxpayer in this case opened an account with a digital currency exchange. He deposited bitcoin into his account in 2013 and 2014. In 2015, he started to liquidate his Bitcoin holdings, which lasted until 2016 when his holdings were depleted. At that [...]

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Sixth Circuit Denies Proceeds Regulation Rehearing Request, Sets Up a Circuit Split

The US Court of Appeals for the Sixth Circuit recently denied a taxpayer’s request for a rehearing en banc in Oakbrook Land Holdings, LLC v. Commissioner, No. 20-2117, leaving a highly contested conservation easement regulation in place and setting up a split between the Sixth and Eleventh Circuits.

In Oakbrook, the taxpayer argued that Treas. Reg. § 1.170A-14(g)(6)(ii), known as the “proceeds regulation,” was invalid because it did not satisfy the Administrative Procedure Act’s (APA) notice-and-comment rulemaking procedures. The regulation addresses how to allocate proceeds between donors and donees if an easement is judicially extinguished and the property is sold. In May 2020, the US Tax Court held that the regulation was “procedurally and substantively valid” under the APA. The Sixth Circuit agreed with the Tax Court, upholding the regulation.

The Sixth Circuit’s order issued July 6, 2022, indicated that neither the judges on the original panel nor any other judge on the full court requested a vote for a suggested rehearing. Last year, however, the Eleventh Circuit reached the opposite conclusion in Hewitt v. Commissioner, finding that the same regulation was invalid because it violated the APA. Thus, there is a clear circuit split on the issue.

Practice Point: The government did not seek a review of the Hewitt decision from the Supreme Court of the United States, so that ruling stands in the Eleventh Circuit. It remains to be seen whether the taxpayer in Oakbrook files a petition for a writ of certiorari to the Supreme Court. With a split between the Sixth and Eleventh Circuits, it is possible this conservation easement battle could be headed to the Supreme Court to determine the fate of the proceeds regulation.




District Court Vacates, Sets Aside IRS Reportable Transaction Notice

The fallout from taxpayer challenges to the Internal Revenue Service’s (IRS) “reportable transaction” regime continues. On March 21, 2022, the district court in CIC Servs., LLC v. IRS ruled in favor of the taxpayer, vacating Notice 2016-66 and ordering the IRS to return all documents and information produced pursuant to Notice 2016-66 to taxpayers and material advisors.

We previously posted about the Supreme Court of the United States’ decision in CIC Servs., LLC v. IRS, which allowed a pre-enforcement challenge to the IRS’s reportable transaction regime. On remand, the parties filed cross-motions for summary judgment. The district court, relying on Mann Construction, Inc. v. United States, explained that the “Sixth Circuit’s analysis in Mann Construction is binding on this Court and applies equally to the arguments advanced by the IRS regarding Notice 2016-66 in this case.” The court dealt the IRS another blow, holding that Notice 2016-66 had to also be set aside as an agency action that was arbitrary and capricious: “[s]imply including cases in the administrative record that suggest certain tax structures could be abusively employed is not synonymous with examining relevant facts and data in connection with issuing the Notice.” In determining the appropriate relief, the court rejected the IRS’s request to limit vacatur of the Notice to CIC, explaining that “vacating the Notice in its entirety is appropriate” and citing the US Court of Appeals for the Sixth Circuit’s prior statement that the IRS “do[es] not have a great history of complying with APA procedures, having claimed for several decades that their rules and regulations are exempt from those requirements” (See CIC Servs., LLC v. IRS, 925 F.3d 247, 258 (6th Cir. 2019) quoting Kristin E. Hickman & Gerald Kersa, Restoring the Lost Anti-Injunction Act, 103 Va. L. Rev. 1683, 1712-13 (2017)).

Practice Point: The assault on the IRS’s reportable transaction regime is far from over. We recently posted about the Sixth Circuit’s opinion in Mann Construction in which it held that Notice 2007-83, which required disclosure of listed transactions relating to certain employee benefit plans, violated the Administrative Procedure Act (APA). APA challenges continue to expand to other IRS notices that bypassed the notice-and-comment requirement, including Notice 2017-10, which identifies certain syndicated conservation easement transactions as listed transactions subject to disclosure to the IRS. These developments will certainly have a significant impact on taxpayers and material advisors’ responsibilities as we move into the tax filing season.




Supreme Court Opens Door to APA Challenge of Overreaching IRS Information Reporting Regime

In CIC Services, LLC v. Internal Revenue Service, a unanimous US Supreme Court allowed CIC, a tax advisor, to proceed with a pre-enforcement challenge to the Internal Revenue Service’s (IRS) “reportable transaction” regime. CIC alleged that the IRS violated the Administrative Procedure Act (APA) when it issued Notice 2016-66 (Notice), deeming certain micro-captive insurance transactions as “reportable transactions” and sought an order enjoining enforcement of the Notice. The IRS sought to avoid judicial review by hiding behind the Anti-Injunction Act’s (AIA) bar on suits brought “for the purpose of restraining the assessment or collection of any tax.” Disagreeing with the trial and appellate courts, the Supreme Court allowed CIC’s suit to proceed, finding that CIC was challenging a regulatory mandate separate from any tax. As the Court explained, “The tax appears on the scene – as criminal penalties do too – only to sanction that mandate’s violation.” By choosing to address their concerns about micro-captive transactions by imposing a non-tax reporting obligation, Congress and the IRS “took suits to enjoin their regulatory response outside the Anti-Injunction Act’s domain.”

On remand, the Court’s decision leaves open questions that the lower courts must now address while also providing meaningful clues about how the Court may approach future disputes over IRS enforcement strategies. Such questions include: (1) does the reportable transaction regime as the IRS currently administers it violate the APA (See: Mann Construction, Inc. v. United States, No. 1:20-cv-11307 (E.D. Mich. May 13, 2021) (holding that IRS Notice requiring disclosure of listed transactions was not subject to APA’s notice-and-comment requirement); (2) would the AIA bar a suit to enjoin enforcement of a reporting obligation brought by a taxpayer, as opposed to an advisor; (3) how onerous must the challenged requirement be; (4) how disconnected from the tax penalty must the challenged requirement be and (5) is the existence of criminal penalties sufficient and/or necessary to exempt a challenge from the AIA?

Practice Point: APA challenges in tax cases have steadily increased since the Supreme Court’s rejection of tax exceptionalism 10 years ago in Mayo Foundation for Medical Education & Research v. United States, 562 U.S. 44 (2011). As tax law continues to get more complicated and the IRS issues additional guidance, we can expect this trend to continue. Understanding how to use the APA to challenge the overreaching of the IRS is an important tool for taxpayers and tax advisors alike. In the absence of a clear congressional mandate, any new enforcement policy issued by the IRS may be fair game for an APA challenge. The Supreme Court has opened the door to judicial review of unsanctioned IRS programs that place unfair burdens on taxpayers. And, this issue extends beyond the reportable transaction regime, including to the information reporting proposals recently announced by the Biden Administration.




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