Dillon Trust Company LLC v. United States, No. 2024-1314 (Fed. Cir. May 14, 2026)

For tax professionals handling the sale of closely held C corporations with highly appreciated assets, balancing the desire for single-level taxation against the risks of transferee liability is a familiar challenge. A recent decision by the United States Court of Appeals for the Federal Circuit, Dillon Trust Company LLC v. United States, serves as a critical cautionary tale. This decision highlights the severe consequences of willful blindness in stock sales to intermediary entities utilizing abusive tax shelters, underscoring that sellers cannot turn a blind eye to economically irrational bids without risking exposure to massive transferee tax liability, penalties, and interest.

Clint L. Martin and Jenifer Martin v. Commissioner of Internal Revenue, T.C. Memo. 2026-40 Stephen Martin and Amanda Martin v. Commissioner of Internal Revenue, T.C. Memo. 2026-39, May 14, 2026

The cases of Martin v. Commissioner center on a pair of cousins, Clint and Stephen Martin, who jointly owned a parcel of land and attempted to donate it to a local municipality. In 2014, Clint Martin successfully bid $22,000 to purchase 13.33 acres of property located in Highland City, Utah. He funded the purchase through Litefoot Investments, LLC, a Utah limited liability company whose members consisted of himself and his cousin, Stephen. In 2016, Clint executed a warranty deed that formally transferred the property into the joint ownership of himself and Stephen.

In 2018, the cousins resolved to donate the property to Highland City. On November 21, 2018, they sent a letter to the mayor and City Council offering the donation. The Highland City Council subsequently voted to accept the property on December 4, 2018. Following this approval, Clint, Stephen, and the mayor of Highland City signed a "Joint Letter" on December 21, 2018. The Joint Letter indicated that the Martins offered "a donation of land" for "[t]he purpose of . . . a conservation contribution" and established an intent for the city "to maintain th[e] property in perpetuity as preserved open space". Furthermore, the letter declared that the property "will be donated" with "all taxes paid and current through the end of 2018" and "all costs associated with said donation . . . paid by the donors".

On December 27, 2018, Clint and Stephen executed a warranty deed conveying the property to Highland City, which was formally recorded alongside the Joint Letter the next day. Crucially, the 2018 deed contained boilerplate language stating that the property was conveyed "for and in consideration of the sum of Ten and no/100 Dollars ($10.00), and other good and valuable consideration in hand paid by" Highland City.

For the 2018 tax year, the property was appraised by Todd Gurney at a valuation of $665,000. On their respective 2018 joint income tax returns, both Clint and Stephen claimed massive charitable contribution deductions—Clint claiming $339,400 (with $332,500 attributable to his 50% interest) and Stephen claiming $332,500 for his 50% interest. Both taxpayers attached Form 8283, Noncash Charitable Contributions, signed by the appraiser, the donors, and the Highland City Administrator, listing their respective bases in the property as $35,000.

“IRS announces terms of a time-limited settlement opportunity for eligible taxpayers involved in conservation easement disputes,” News Release IR-2026-65, May 13, 2026

On May 13, 2026, the Internal Revenue Service issued News Release IR-2026-65, announcing a "time-limited settlement opportunity for eligible taxpayers involved in conservation easement or historic preservation easement disputes with the IRS". As practitioners representing partnerships and investors in these transactions are acutely aware, the scrutiny surrounding deductions for qualified conservation contributions—governed by I.R.C. § 170(h)(1)—has intensified. This settlement initiative alters the landscape for resolving protracted disputes, offering structured terms that diverge from prior IRS settlement programs.

REG-118484-25, May 11, 2026

The Department of the Treasury, the Internal Revenue Service (IRS), the Department of Labor, and the Department of Health and Human Services recently issued proposed regulations to amend 26 CFR Part 54, as well as corresponding regulations under ERISA and the Public Health Service (PHS) Act. The primary objective of these proposed rules is to establish specific fertility benefits as a new classification of "limited excepted benefits". By classifying these benefits as excepted benefits, they become "generally exempt from the market requirements" found in Chapter 100 of the Internal Revenue Code, Part 7 of ERISA, and Title XXVII of the PHS Act.

The rationale for this regulatory action is deeply rooted in demographic trends and recent executive policy directives. The preamble explicitly highlights a demographic shift, noting that the United States is currently experiencing a declining fertility rate where the "general fertility rate declined by 14 percent" between 2014 and 2024, remaining "below replacement level for over a decade". The total fertility rate has dropped to 1.6 births per woman in 2023, which is below the 2.1 replacement level necessary for a population to sustain itself.

Furthermore, the regulations are a direct response to Executive Order 14216, "Expanding Access to In Vitro Fertilization," which established that "as a Nation, our public policy must make it easier for loving and longing mothers and fathers to have children". The Executive Order seeks to ensure reliable access to in vitro fertilization (IVF) by "easing unnecessary statutory or regulatory burdens to make IVF treatment drastically more affordable". Separately, the regulations align with Executive Order 14192, "Unleashing Prosperity Through Deregulation," which prioritizes efforts to "alleviate unnecessary regulatory burdens placed on the American people".

Historically, most employer-sponsored major medical health plans have not covered fertility treatments, and where employers do offer such coverage, "many have claims for such benefits administered under a separate contract from their major medical coverage". The Departments recognize that "coverage for the diagnosis, mitigation, or treatment of infertility or infertility-related reproductive health conditions" is lacking and hope that creating this new limited excepted benefit will "reduce the regulatory burden for employers seeking to offer fertility benefits to their employees".

The State of Oregon, et al. v. United States, and Burlap and Barrel, Inc., et al. v. United States, Slip Op. 26-47 (Ct. Int'l Trade May 7, 2026).

For certified public accountants (CPAs) and enrolled agents (EAs) advising clients engaged in international commerce, sudden shifts in trade policy and the imposition of import surcharges present significant tax and cash-flow implications. The United States Court of International Trade (CIT) recently addressed the legality of a broad 10 percent ad valorem tariff imposed by the Executive Branch. This article provides a technical analysis of the CIT's opinion, detailing the factual background, the plaintiffs' request for relief, the court's statutory interpretation, the application of the law, and the ultimate conclusions regarding the President's authority under Section 122 of the Trade Act of 1974.

Dunlap v. United States, US District Court, Southern District New York, No. 1:25-cv-02942, (May 6, 2026)

For tax practitioners, the intersection of timely filing rules and federal court jurisdiction is a critical area of tax administration. The recent decision in Dunlap v. United States serves as a stark reminder of the evidentiary burdens taxpayers face when relying on the "timely mailing treated as timely filing" rule under Internal Revenue Code (IRC) § 7502. This article examines the facts, legal analysis, and conclusions of the United States District Court for the Southern District of New York regarding jurisdictional time bars for refund claims.

Revenue Procedure 2026-21, May 5, 2026

For tax practitioners handling complex corporate transactions, securing a Private Letter Ruling (PLR) from the Internal Revenue Service (IRS) is often a critical step in managing tax risk. Recently, the IRS released Revenue Procedure 2026-21, 2026-22 I.R.B. 1, which establishes "a program for letter rulings with respect to certain issues solely under the jurisdiction of the Associate Chief Counsel (Corporate)". This article analyzes the purpose of this newly reinstated significant issue program, its historical context, the taxpayers it impacts, and the procedural mechanics and limitations governing its use.

Daines v. IRS, No. 24-CV-1057 (E.D. Wis. May 4, 2026)

The dispute in this case centered around the implementation and operation of an employee stock ownership plan (ESOP). The individual plaintiffs, Jeffrey and Elisha Daines and Jeffrey and Stephanie Federwitz, alongside their corporate entities Solid Ground Inc. and Solid Ground Transportation, Inc., sought to establish an ESOP to take advantage of specific tax benefits. To execute this strategy, the taxpayers enlisted Lex J. Byers and his company, who aggressively marketed "a proprietary system that would afford certain tax benefits". This arrangement created the seventh plaintiff in the case, the Solid Ground Transportation Inc. Employee Stock Ownership Plan.

Xavier Garcia-Rojas et al. v. Franchise Tax Board, A172054, California Court of Appeal, First Appellate District, Division Three, May 1, 2026

On May 1, 2026, the California Court of Appeal, First Appellate District, delivered a significant decision impacting nonresident taxpayers in Xavier Garcia-Rojas et al. v. Franchise Tax Board. The court evaluated whether a nonresident independent contractor operating as a sole proprietor constitutes a unitary business subject to California income apportionment.

Kimberly Road Fulton 25, LLC v. Commissioner and South Fulton Parkway 58, LLC v. Commissioner, T.C. Memo. 2026-36, May 4, 2026

The United States Tax Court recently handed down a memorandum decision in the consolidated cases of Kimberly Road Fulton 25, LLC v. Commissioner and South Fulton Parkway 58, LLC v. Commissioner, T.C. Memo. 2026-36. Governed by the Tax Equity and Fiscal Responsibility Act of 1982 (TEFRA), this case highlights the critical importance of a realistic Highest and Best Use (HBU) analysis and the limits of the comparable sales method when appraising properties for Internal Revenue Code (IRC) § 170(h) charitable deductions. While the taxpayers successfully defended the procedural validity and conservation purposes of their easements, they were ultimately defeated by vastly overstated appraisals that resulted in severe valuation misstatement penalties.

Executive Order, “Promoting Retirement-Savings Access For American Workers By Establishing TrumpIRA.gov,” April 30, 2026

On April 30, 2026, the Executive Order "Promoting Retirement-Savings Access for American Workers by Establishing TrumpIRA.gov" was signed to address a significant coverage gap in the United States retirement system. For tax professionals, understanding the mechanisms of this order is critical, as it directly bridges gaps in retirement planning for self-employed and gig-economy clients by utilizing the Federal Saver’s Match enacted under the SECURE 2.0 Act.

The stated reason for the order is straightforward: "Tens of millions of Americans lack access to employer-sponsored retirement plans". The administration notes that "Workers in small businesses, part-time workers, independent contractors, and self-employed workers face unnecessary barriers to saving for retirement". The explicit policy goal is to "establish an easy and transparent way for eligible workers to obtain up to a $1,000 match for their savings", offering these workers "portable savings vehicles that offer access to low-cost investments similar to those offered to Federal workers in the Thrift Savings Plan".

Proposed Regulations (REG-119294-25) and Temporary Regulations (T.D. 10047), April 30, 2026

The enactment of the One, Big, Beautiful Bill Act (OBBBA) introduced Internal Revenue Code (IRC) Section 6435, providing a mechanism for recovering the Section 4081 excise tax paid on diesel fuel or kerosene that subsequently qualifies as exempt under Section 4082(a). Recently, the Department of the Treasury and the Internal Revenue Service (IRS) issued temporary regulations (T.D. 10047) and cross-referenced proposed regulations (REG-119294-25) addressing these payments. The IRS also issued a corresponding news release, IR-2026-59, to announce "a new method for recovering federal excise tax paid on dyed fuel established under the One, Big, Beautiful Bill".

“Treasury, IRS Announce Process for Tax Guidance Following DOJ Final Order on Medical Marijuana Rescheduling,” US Treasury Website, April 23, 2026

Following the final order issued by the Department of Justice (DOJ) and the Drug Enforcement Administration (DEA) to reschedule certain marijuana products from Schedule I to Schedule III of the Controlled Substances Act (CSA), the U.S. Department of the Treasury and the Internal Revenue Service (IRS) issued a press release on April 23, 2026, detailing the forthcoming tax guidance. This administrative shift carries substantial tax implications for clients operating in the cannabis space, directly impacting the application of the deduction disallowance under Section 280E of the Internal Revenue Code (I.R.C.).

For tax practitioners, analyzing the Treasury's initial statements against the DEA’s regulatory recommendations is critical for effective tax planning in the coming filing seasons.

House Floor Action Passing Bills, April 27, 2026

As tax professionals, staying abreast of statutory changes to the Internal Revenue Code (IRC) is essential for accurate advisory and compliance work. On April 27, 2026, the House of Representatives advanced a suite of nine bipartisan tax administration bills. 

The nine bills passed by the House are as follows:

• H.R. 6495, titled the Taxpayer Notification and Privacy Act.

• H.R. 227, titled the Clergy Act.

• H.R. 6431, titled the New Opportunities for Business Ownership and Self-Sufficiency Act.

• H.R. 6956, titled the Barcode Automation for Revenue Collection to Organize Disbursement and Enhance Efficiency Act (or the BARCODE Efficiency Act).

• H.R. 2347, titled the Survivor Justice Tax Prevention Act.

• H.R. 5366, titled the Doug LaMalfa Federal Disaster Tax Relief Certainty Act.

• H.R. 5334, titled the Supporting Early-childhood Educators’ Deductions Act (or the SEED Act).

• H.R. 7971, titled the Taxpayer Experience Improvement Act.

• H.R. 7959, titled the IRS Whistleblower Program Improvement Act.

According to a Tax Notes article authored by Katie Lobosco and Cady Stanton, these bills were passed through a fast-track procedure typically reserved for noncontroversial legislation requiring a two-thirds majority vote. However, the Tax Notes authors also observed that the fate of these bills remains unclear in the Senate, where taxwriters have introduced a broader tax administration package (S. 3931).

“IRS announces new option for certain taxpayers to request more time after ERC claim disallowance,” IR-2026-58, April 27, 2026

As tax professionals are well aware, when the Internal Revenue Service disallows an Employee Retention Credit (ERC) claim, the taxpayer receives either a Letter 105-C for a full disallowance or a Letter 106-C for a partial disallowance. Upon receipt of these legal notices, affected taxpayers "generally have two years from the date of that letter to resolve their claim administratively or to file a refund suit in Federal court if they disagree with the IRS's decision". However, practitioners must caution their clients that electing to protest the disallowance with the IRS Independent Office of Appeals "does not extend this statutory two-year deadline". By statute, the Service notes that it "can't issue a refund or allow a credit after the two-year period unless you file suit during that period". Consequently, the IRS emphasizes that "If you do not file suit within the 2-year period, or do not enter into a written extension agreement before it expires the IRS cannot issue a refund or credit, even if Appeals later issues a favorable decision". Without a formal extension, the taxpayer's only recourse to preserve their claim is to "File suit with the U.S. District Court that has jurisdiction or with the U.S. Court of Federal Claims".

Chief Counsel Advice 202617012 (Apr. 24, 2026).

For tax practitioners advising foreign-owned domestic corporations, the reporting and record-maintenance requirements of I.R.C. § 6038A represent a critical compliance area with severe financial consequences for failures. Under I.R.C. § 6038A(a) and (b), any domestic corporation that is at least 25-percent foreign-owned must file an information return (Form 5472) to report transactions with related parties and must maintain records appropriate to determine the correct tax treatment of those transactions. If a reporting corporation fails to furnish this information or maintain these records, I.R.C. § 6038A(d)(1) mandates that "such corporation shall pay a penalty of $25,000 for each taxable year with respect to which such failure occurs".

Taxpayers may be excused from these penalties under the reasonable cause exception found in I.R.C. § 6038A(d)(3) and Treas. Reg. § 1.6038A-4(b). Generally, an affirmative showing must be made under penalties of perjury that the taxpayer acted in good faith and had reasonable cause for the failure. Recognizing that these requirements may disproportionately impact smaller entities, the Treasury Regulations contain a specific small-corporation provision (SCP). Treas. Reg. § 1.6038A-4(b)(2)(ii) instructs that the IRS "shall apply the reasonable cause exception liberally in the case of a small corporation".

Chief Counsel Advice (CCA) 202617012 was issued by the Office of Associate Chief Counsel (International) in response to a request from the Independent Office of Appeals. Because it is a CCA rather than a judicial court opinion, it does not adjudicate a specific taxpayer's dispute; rather, the memorandum is meant to address the administrative situations in which IRS personnel must evaluate a small corporation's claim for penalty relief under the SCP.

Department of Justice, Drug Enforcement Administration, 21 C.F.R. Parts 1300, 1301, 1308, 1312, Docket No. DEA-XXXX, Attorney General Order XXXX-XXXX, Schedules of Controlled Substances: Rescheduling of Food and Drug Administration Approved Products Containing Marijuana and Products Containing Marijuana Subject to a Qualifying State-issued License From Schedule I to Schedule III; Corresponding Change to Permit Requirements (effective Apr. 22, 2026).

For tax professionals advising clients in the cannabis industry or individual taxpayers with substantial medical expenses, the April 22, 2026, final order by the Drug Enforcement Administration (DEA) represents a seismic shift in the application of federal tax law. By transferring specific marijuana products from Schedule I to Schedule III of the Controlled Substances Act (CSA), the order bifurcates the tax treatment of state-legal marijuana businesses and opens new avenues for individual medical deductions.

This article examines the technical application of I.R.C. § 280E and I.R.C. § 213 following this final order.

Estate of Kurt A. Amplatz v. Commissioner, T.C. Memo. 2026-35.

In 2014, Kurt A. Amplatz formed KA Medical, LLC (KA Medical), a medical device company. Through the Medical Trust, Mr. Amplatz contributed $500,000 for 500,000 membership units. Furthermore, a separate entity, the Funding Trust, transferred approximately $19 million to KA Medical for research and development in exchange for promissory notes. Between 2015 and 2018, KA Medical generated no revenue, and no principal or interest payments were made on the promissory notes.

Mr. Amplatz passed away on November 6, 2019. Less than a year later, in July 2020, the company received a nonbinding letter of intent from a buyer to purchase KA Medical for $15 million. However, relying on an independent appraisal from Value Consulting Group dated July 20, 2020, the Estate filed Form 706, selecting an alternate valuation date of May 6, 2020, and reported the value of its membership units in KA Medical at zero and the promissory notes at $1 million. In November 2020, the Estate formally sold all membership units in KA Medical to the buyer for $15 million.

The Internal Revenue Service (IRS) subsequently examined the Estate's Form 706 and adjusted the value of KA Medical to $15,145,000, while alternately valuing the promissory notes at either zero (treated as equity) or $17,686,508. The IRS issued a Notice of Deficiency determining an estate tax deficiency of $5,686,714 and assessed accuracy-related penalties under I.R.C. § 6662 totaling $2,423,200.

Hyatt Hotels Corporation & Subsidiaries v. Commissioner of Internal Revenue, No. 24-3239 (7th Cir. Apr. 22, 2026)

Hyatt Hotels Corporation operates a global hospitality brand that encompasses owned, managed, and franchised properties. During the 2009 through 2011 tax years under scrutiny, Hyatt operated a customer loyalty program known as the Gold Passport Program, which was mandatory for all Hyatt-branded hotels, including the 75-80% of properties owned by third-party franchisees. Members earned reward points that could be redeemed for hotel stays, perks, or airline miles.

To fund the costs of this program, Hyatt maintained the Gold Passport Fund (the Fund). Third-party hotel owners were required to remit 4% of qualifying purchases into the Fund when points were issued, or the actual cost of airline miles if the guest elected that reward. The Fund additionally accumulated revenue from investments in securities and from the direct sale of reward points to customers. Hyatt utilized the Fund to compensate hotel owners when points were redeemed and to cover administrative and advertising expenses. Historically, since the program's inception in 1987, Hyatt essentially disregarded the Fund for tax purposes. However, in March 2017, the IRS issued a notice of deficiency, contending that the payments remitted to the Fund by third-party owners, as well as revenue from direct point sales and investment holdings, should have been reported as gross income to Hyatt. The IRS took the position that Hyatt could only deduct the costs of redeemed points in the year of actual redemption.

Cathryn A. Simmons v. Commissioner, T.C. Memo. 2026-34 (April 22, 2026)

In a recent memorandum decision, the United States Tax Court addressed recurring substantiation issues surrounding closely held entities, commingled funds, and rental real estate deductions. The taxpayer, Cathryn A. Simmons, petitioned the Tax Court to challenge deficiency determinations issued by the Internal Revenue Service (IRS) for the 2017 and 2019 tax years, alongside a 20% accuracy-related penalty assessed under Internal Revenue Code (I.R.C.) section 6662(a) for the 2017 tax year. Following several IRS concessions prior to and following trial, the remaining issues centered on whether Ms. Simmons adequately substantiated business deductions for a partnership she co-owned, deductible expenses associated with two rental properties, and whether she qualified for the reasonable cause exception to negate the accuracy-related penalty.