The United States Tax Court recently issued T.C. Memo. 2025-81, Kadau v. Commissioner, a ruling for navigating the complexities of microcaptive insurance arrangements. This case, involving Curtis K. Kadau and Surface Engineering & Alloy Co., Inc. (an S corporation of which Mr. Kadau was the sole shareholder), delves into the deductibility of expenses for purported insurance coverage provided through affiliated captive insurance companies, Risk & Asset Protection Services, Ltd. (Risk & Asset) and RMC Property & Casualty, Ltd. (RMC Property). The Internal Revenue Service (IRS) challenged the arrangement, asserting that it did not constitute actual insurance, thus disallowing deductions and imposing accuracy-related penalties.

Understanding the intricate nuances of tax exemptions for nonprofit organizations is crucial for those involved with tax exempt clients. A recent decision from the United States Court of Appeals for the Eighth Circuit, Mayo Clinic v. United States (Case No. 23-2246), provides significant clarity, particularly concerning the definition of an "educational organization" under Internal Revenue Code (IRC) § 170(b)(1)(A)(ii) and its implications for unrelated business income tax (UBIT) exemptions. This article delves into the factual background, the taxpayer’s request for relief, the court’s detailed legal analysis, and its application to Mayo Clinic’s operations, culminating in the court’s conclusions.

The United States Court of Appeals for the Fourth Circuit recently addressed a critical issue for corporate tax professionals regarding the application of the interest netting provision under 26 U.S.C. § 6621(d) following a corporate merger. This case, Bank of America Corporation v. United States (CA4, Case No. 23-2319) provides essential clarity on the interpretation of the “same taxpayer” requirement for pre-merger underpayments and overpayments.

The Corporate Alternative Minimum Tax (CAMT), introduced by the Inflation Reduction Act of 2022, has presented significant compliance challenges, particularly concerning partnership investments. In response to these burdens and associated costs, the Department of the Treasury (Treasury Department) and the Internal Revenue Service (IRS) have issued Notice 2025-28. This notice provides crucial interim guidance, signaling a partial withdrawal of the CAMT proposed regulations and the intent to issue revised proposed regulations, incorporating rules similar to those outlined in the notice. Taxpayers may rely on this interim guidance, which aims to simplify the application of CAMT to partnerships and CAMT entity partners.

The upcoming tax filing season is expected to get off to a late start, with the IRS aiming to begin to accept returns somewhere around the President’s Day (February 17, 2026), per a statement made by IRS Commissioner Billy Long at the National Association of Enrolled Agents Tax Summit on July 28, 2025.  The statement was reported in a story about the event published in Tax Notes Today Federal.

The recent Tax Court Memorandum decision in Adrienne Mennemeyer v. Commissioner of Internal Revenue, T.C. Memo. 2025-80, offers valuable insights for tax professionals regarding the taxability of settlement proceeds, the deductibility of business expenses, and the imposition of penalties for failure to timely file. This case underscores the critical importance of meticulous record-keeping and clear documentation in substantiating claims before the Internal Revenue Service (IRS) and the Tax Court.

The Large Business and International (LB&I) Division has announced significant modifications to its examination process, outlined in a recent memorandum effective August 1, 2025. These changes are intended to foster more efficient and effective examinations, enhance taxpayer service, and promote collaborative issue resolution. This article will delve into the procedural updates concerning the elimination of the Acknowledgment of Facts (AOF) Information Document Request (IDR), the updated Fast Track Settlements (FTS) pilot program, and clarifications regarding the applicability of Accelerated Issue Resolution (AIR) to Large Corporate Compliance (LCC) cases.

Staying abreast of changes to the Affordable Care Act’s (ACA) Employer Shared Responsibility Provisions (ESRP) under Internal Revenue Code (IRC) Section 4980H is crucial for advising applicable large employers (ALEs). The Internal Revenue Service (IRS) recently released Rev. Proc. 2025-26, providing the indexing adjustments for the upcoming calendar year 2026. This article will detail the foundational elements of the ESRP, outline the recent adjustments, and discuss other key administrative considerations.

The recent decision in Carole Nicholson v. United States of America, USDC ND FL, Case No. 3:24-cv-00603, serves as a reminder for tax professionals regarding the strict procedural requirements for tax refund claims. This case underscores the jurisdictional prerequisites that must be satisfied before a federal court can hear a taxpayer’s suit against the Internal Revenue Service (IRS), particularly concerning the proper forms and timeliness of administrative claims.

In the realm of tax practice, the substantiation of deductions often proves to be a contentious area, particularly with noncash charitable contributions. The recent Tax Court Summary Opinion in John Henry Besaw v. Commissioner, T.C. Summary Opinion 2025-7, Docket No. 19222-22S (July 21, 2025), provides a stark reminder of the meticulous record-keeping required to preserve these deductions. This case underscores the importance of adhering strictly to statutory and regulatory substantiation rules, even when the underlying charitable intent is not disputed.

Tax professionals must remain apprised of the annual adjustments to critical provisions governing the Affordable Care Act (ACA), particularly those affecting the premium tax credit (PTC) under Internal Revenue Code (Code) §36B and the affordability of employer-sponsored health coverage. Rev. Proc. 2025-25, 2025-32 IRB 1, issued by the Internal Revenue Service (IRS) and the Department of the Treasury, provides these essential indexing adjustments for taxable years and plan years beginning in calendar year 2026. This revenue procedure supplements Rev. Proc. 2014-37, 2014-2 C.B. 363, which outlined the original methodology for these adjustments.

The United States Court of Appeals for the Fifth Circuit recently affirmed the Tax Court’s decision disallowing tax deductions for insurance premium payments made by Dr. Bernard T. Swift’s medical practice to his captive insurance companies and upholding associated penalties. This case, Bernard T. Swift, Jr.; Kathy L. Swift v. Commissioner of Internal Revenue, No. 24-60270, provides crucial insights into the criteria for genuine insurance arrangements and the application of accuracy-related penalties in the context of micro-captive transactions.

Revenue Ruling 2025-15 provides crucial clarification for plan administrators and tax professionals regarding federal income tax withholding and reporting obligations when retirement plan distribution checks remain uncashed and subsequent checks are issued. This analysis delves into the facts presented in the ruling, the Internal Revenue Service’s (IRS) legal interpretation, its application to the specific scenario, and the definitive rules established.

Tax professionals are continually challenged by the complexities surrounding conservation easement valuations, a recurring point of contention with the Internal Revenue Service. The recent Tax Court case, Veribest Vesta, LLC v. Commissioner of Internal Revenue, Docket No. 9158-23, provides valuable insights into the Court’s scrutiny of claimed deductions for such easements, particularly when valuations appear overly optimistic or lack sufficient market support. This article will delve into the facts of this case, the taxpayer’s request for relief, the legal analysis, the application of law to the facts, and the Court’s ultimate conclusions.

As tax professionals, we frequently encounter statutory deadlines that dictate our clients’ rights and our obligations. One area of particular interest, especially following a significant Supreme Court ruling, is the doctrine of equitable tolling as it applies to the Tax Court’s filing deadlines. The recent oral findings of fact and opinion in Boechler, P.C. v. Commissioner of Internal Revenue, Docket No. 18578-17L (Bench Opinion June 12, 2025), provides a practical application of this doctrine following its remand from the United States Court of Appeals for the Eighth Circuit. This article will delve into the specifics of this case, outlining the factual background, the taxpayer’s plea for relief, the court’s legal analysis of equitable tolling, and its ultimate conclusions.

The United States Tax Court’s decision in Estate of Billy S. Rowland, Deceased, James A. Park, Executor v. Commissioner of Internal Revenue, T.C. Memo. 2025-76, provides critical insights for tax professionals concerning the deceased spousal unused exclusion (DSUE) amount and the stringent requirements for electing portability. This case underscores the importance of strict compliance with filing deadlines and return preparation standards, even when attempting to utilize administrative safe harbors.

The recent decision in Rock Cliff Reserve, LLC v. Commissioner, T.C. Memo. 2025-73, offers crucial insights for tax professionals navigating the complexities of conservation easement deductions and related penalties. This memorandum opinion addresses consolidated cases involving four partnerships—Rock Cliff Reserve, LLC (Rock Cliff PropertyCo), Jack’s Creek Reserve, LLC (Jack’s Creek PropertyCo), East Village Reserve, LLC (East Village PropertyCo), and Baker’s Farm Nature Reserve, LLC (Baker’s Farm PropertyCo), collectively referred to as the PropertyCos. Five Rivers Conservation Group, LLC (Five Rivers), served as the tax matters partner for each. The case scrutinizes charitable contribution deductions claimed for conservation easements, totaling over $62 million, along with "Other Deductions" claimed in Walton County, Georgia, for the 2015 tax year.

Tax professionals who advise tax-exempt organizations are aware of the stringent rules governing political activity, particularly for entities described under Internal Revenue Code (IRC) Section 501(c)(3). A significant legal development is currently under consideration by the United States District Court for the Eastern District of Texas: a proposed consent judgment in the case of National Religious Broadcasters, et al. v. Billy Long, et al., which addresses the interpretation of the "Johnson Amendment" as it applies to churches. This proposed agreement, while not yet binding, offers crucial insights into the ongoing dialogue surrounding religious organizations' political speech and their tax-exempt status.

For experienced tax professionals, understanding the mechanisms for tax relief during unforeseen events is paramount. Internal Revenue Code (IRC) Section 7508A currently provides the Secretary of the Treasury with broad authority to postpone certain tax-related deadlines due to specific types of disasters and actions. However, a recently passed bill, the "Filing Relief for Natural Disasters Act" (H.R. 517), passed by both the House and the Senate, aims to significantly expand the scope and duration of this relief. This article details the existing provisions of Section 7508A and illuminates the key modifications this bill would introduce if enacted.  The bill was awaiting the President’s signature at the time this article was written.

Tax professionals understand that jurisdiction is a foundational element for any case brought before the United States Tax Court. As a court of limited jurisdiction, the Tax Court may only exercise authority granted by Congress. A recent memorandum opinion, Donna Davis v. Commissioner, T.C. Memo. 2025-72, offers a critical reminder of the stringent requirements for establishing jurisdiction, particularly concerning the validity of a Notice of Deficiency and the timely filing of a petition. This case underscores the importance of adherence to procedural rules, even in the face of sympathetic circumstances.