The Treasury Department and the IRS have finalized regulations (TD 10037) providing definitive guidance on the application of the stock repurchase excise tax, enacted under section 10201 of the Inflation Reduction Act of 2022 (IRA). These final regulations, which amend 26 CFR parts 1 and 58, are effective on November 24, 2025. They affect domestic publicly traded corporations and their specified affiliates for repurchases made after December 31, 2022. This technical guidance is issued pursuant to the express delegations of authority found in sections 1275(d), 4501(f), and 7805(a) of the Code.

The enactment of section 139L of the Internal Revenue Code (Code) by Public Law 119-21, 139 Stat. 72 (July 4, 2025), known as the One, Big, Beautiful Bill Act (OBBBA), created a new partial exclusion from gross income for certain interest received by qualified lenders. Notice 2025-71 has been issued by the Treasury Department and the Internal Revenue Service (IRS) to provide crucial interim guidance on the application of this provision. This article outlines the statutory requirements, details the administrative positions provided in the Notice, and clarifies the reliance standards for tax professionals advising qualified lenders.

This article examines the decision in United States of America v. Tuncay Saydam, Case No. 22-cv-07371-DMR, issued by the United States District Court for the Northern District of California. The case centers on the application of the Excessive Fines Clause of the Eighth Amendment to willful civil penalties imposed for failure to file Reports of Foreign Bank and Financial Accounts (FBARs).

This article examines the decision in Tom Prescott v. Commissioner of Internal Revenue, T.C. Memo. 2025-121 (2025), focusing on the technical requirements for establishing a mandatory whistleblower award under Internal Revenue Code (I.R.C.) section 7623(b) and the corresponding Treasury Regulations. The case hinges on whether the information provided by the petitioner "substantially contributed" to the resulting administrative action and collection of proceeds, especially in the context of multiple independent whistleblower claims.

This article examines the recent Tax Court Memorandum decision in John DiTullio v. Commissioner of Internal Revenue, T.C. Memo. 2025-120, concerning the critical requirement under pre-Tax Cuts and Jobs Act (TCJA) law that alimony payments terminate upon the death of the payee spouse to qualify for a deduction under Section 215(a). This case highlights the necessity of explicit termination provisions, especially where state law regarding maintenance obligations is deemed ambiguous.

On November 14, 2025, the Centers for Medicare & Medicaid Services (CMS) released the finalized amounts for premiums, deductibles, and coinsurance under the Medicare Part A and Part B programs for the 2026 calendar year, concurrently announcing the Medicare Part D income-related monthly adjustment amounts (IRMAA). This technical brief reviews the statutory context and the specific figures relevant to client planning for 2026, focusing particularly on the impact of modified adjusted gross income (MAGI) thresholds on Part B and Part D premiums.

The recent decision in Jodell Sample v. Commissioner of Internal Revenue, T.C. Memo. 2025-118, presents a complex application of Internal Revenue Code (I.R.C.) § 6015, particularly concerning the interaction of knowledge standards across subsections (b), (c), and (f) relief, and the critical role of the administrative record in a stipulated Tax Court case. This analysis details the facts, the scope of the taxpayer’s requests for relief from joint and several liability, and the court’s strict application of statutory and procedural standards.

The case, Apache Corporation and Subsidiaries v. Commissioner of Internal Revenue, 165 T.C. No. 11 (2025), addressed a critical issue concerning the elective relinquishment of net operating loss (NOL) carryback periods under I.R.C. § 172.

The Internal Revenue Service (IRS) issued Notice 2025-67 to announce the cost-of-living adjustments (COLAs) that will take effect on January 1, 2026, for the limitations pertaining to qualified retirement plans and Individual Retirement Arrangements (IRAs). This guidance is essential for tax professionals and plan administrators to determine the correct compliance thresholds and maximum contribution levels for the upcoming plan year.

The United States Tax Court, in Pascucci v. Commissioner, T.C. Memo. 2024-43 (Apr. 15, 2024), and subsequently the United States Court of Appeals for the Second Circuit in Pascucci v. Commissioner of Internal Revenue, No. 24-2429 (2d Cir. Nov. 12, 2025) (Summary Order), addressed the critical question of property ownership in the context of a claimed theft loss deduction stemming from the Bernard L. Madoff Ponzi scheme. The courts determined that indirect investors in variable life insurance policies, though victims of the underlying fraud, lacked the requisite property interest in the stolen funds necessary to sustain a deduction under I.R.C. § 165(c)(3).

Updated November 13 to add discussion of threshold relevancy determination.

The United States Tax Court, in Sunil S. Patel and Laurie McAnally Patel, et al. v. Commissioner of Internal Revenue, 165 T.C. No. 10 (2025), addressed the imposition of accuracy-related penalties following its determination in Patel v. Commissioner, T.C. Memo. 2024-34 (Patel II), that amounts paid to purported captive insurance companies Magellan and Plymouth, and to the reinsurer Capstone Reinsurance Co., Ltd. (Capstone), were not insurance premiums for federal income tax purposes. This Opinion specifically resolves the remaining issue: whether Petitioners (Ps) are liable for various accuracy-related penalties under I.R.C. § 6662(a), including penalties predicated on the codified economic substance doctrine under I.R.C. § 7701(o). The relevant tax years at issue are 2013, 2014, 2015, and 2016.

The Internal Revenue Service (IRS) and the Department of the Treasury have issued Rev. Proc. 2025-31 to provide a safe harbor for trusts seeking to engage in the staking of digital assets while maintaining their favorable classification as investment trusts under § 301.7701-4(c) and as grantor trusts for Federal income tax purposes. This procedure addresses the critical question of whether staking activities constitute a "business" enterprise or grant the trust a prohibited "power to vary the investment," either of which could lead to reclassification as an association taxable as a corporation.

The implementation of digital asset reporting requirements, stemming from the changes to Internal Revenue Code (IRC) §6045 enacted by the Infrastructure Investment and Jobs Act (IIJA), marks a significant operational shift for brokers. Treasury and the IRS have published final regulations requiring reporting on dispositions of digital assets in certain sale or exchange transactions, effective for transactions occurring on or after January 1, 2025, utilizing Form 1099-DA. The Internal Revenue Service (IRS) recently issued Frequently Asked Questions (FAQs) that clarify several technical nuances relevant to compliance and implementation, particularly concerning the scope of reporting, utilization of customer acquisition data, and exceptions related to transaction fees and stablecoins.

As tax professionals advising clients on charitable contributions and partnership taxation, the recent decision by the Sixth Circuit in Corning Place Ohio, LLC v. CIR, No. 25-1093, decided and filed November 5, 2025, serves as a critical reminder regarding the strict observance of timing rules, valuation standards, and documentation requirements. The court affirmed the Tax Court’s decision to disallow a significant conservation easement deduction and uphold severe penalties.

The oral arguments in Learning Resources, Inc., et al. v. Donald J. Trump, President of the United States, et al. (No. 24-1287) focused on three primary areas of legal dispute: the interpretation of the statutory text of the International Emergency Economic Powers Act (IEEPA), the applicability of constitutional doctrines like the Major Questions Doctrine (MQD) and the Nondelegation Doctrine (NDD), and the scope of the President's authority in foreign affairs and national emergencies [6:15-18, 55:7-12].

Notice 2025-62 provides crucial penalty relief specifically for taxable year 2025 regarding new information reporting mandates enacted by Public Law 119-21, 139 Stat. 72 (July 4, 2025), commonly referred to as the One, Big, Beautiful Bill Act (OBBBA). This relief addresses potential failures related to implementing the new reporting requirements for deductions related to qualified tips (new Code section 224) and qualified overtime compensation (new Code section 225). The relief targets penalties imposed under section 6721 for failure to file correct information returns and under section 6722 for failure to furnish correct payee statements.

This article examines the decision reached by the Office of Tax Appeals (OTA) in In the Matter of the Appeal of: J. Lunt, OTA Case No. 230112468, concerning a proposed assessment of additional tax, a late filing penalty, and applicable interest for the 2018 tax year. The case provides guidance regarding the respective burdens of proof borne by the Franchise Tax Board (FTB) and the taxpayer when residency and income sourcing are disputed, and an initial return was never filed. The FTB proposed an assessment totaling $12,315 in tax and a late filing penalty of $3,078.75, plus interest.

This article analyzes the standards and application of 26 U.S.C. § 6672 concerning the Trust Fund Recovery Penalty (TFRP) as determined by the United States District Court for the Eastern District of Pennsylvania in United States of America v. Kathryn S. Flaim. The court granted the Government’s Motion for Summary Judgment, finding the defendant liable for unpaid federal employment taxes totaling $204,466.54 (as of September 29, 2025). This analysis focuses on the court’s determination that the taxpayer qualified both as a "responsible person" and acted "willfully" in failing to remit trust fund taxes.

The memorandum opinion in Paul-Adams Quarry Trust, LLC, Francis L. Adams, Tax Matters Partner, v. Commissioner Of Internal Revenue, T.C. Memo. 2025-112, addresses the proper valuation of a qualified conservation contribution under Internal Revenue Code (I.R.C.) § 170(h), specifically focusing on whether the highest and best use of the property supported the substantial charitable deduction claimed, and whether accuracy-related penalties applied.

The distinction between ordinary income and capital gains remains paramount in federal taxation. Taxpayers often seek to characterize income as capital gains, which are frequently taxed at lower rates than ordinary income, such as interest. Congress enacted 26 U.S.C. § 483 in 1964 specifically to combat the practice of taxpayers converting what should be ordinary interest income into capital gain by structuring installment contracts without explicitly providing for interest payments. Section 483 ensures that if a deferred payment on a sale or exchange of property fails to provide adequate stated interest, a portion of that payment is imputed as "unstated interest" and taxed as ordinary income.

A recent decision from the United States Court of Appeals for the Third Circuit addresses the application of this statute in the context of a short-form merger settlement. In Trust Under the Trust of Charles G. Berwind Trust, F/B/O David M. Berwind, Jr., et al. v. Commissioner of Internal Revenue, the Third Circuit affirmed the Tax Court’s decision, concluding that the $191 million settlement payment received by the minority shareholder trusts (collectively, the "DB Trust") must include an imputed interest component under Section 483.