Disguised Sales and Sham Partnerships: A Comprehensive Review of PICCIRC, LLC v. Commissioner

As tax professionals, understanding the nuances of partnership taxation, particularly in distressed asset transactions, is crucial. The recent affirmations in PICCIRC, LLC and PIMLICO, LLC v. Commissioner provide critical insights into how courts scrutinize structured transactions and apply anti-abuse doctrines. This article will dissect the United States Tax Court’s original holding and the subsequent affirmance by the Second Circuit Court of Appeals, highlighting key legal interpretations and their practical implications.

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Denham Outlines Its Criticisms of the Tax Court’s Use of the Functional Analysis Test for Limited Partners with the First Circuit Court of Appeals

The core of the dispute revolves around the application of the limited-partner exception found in 26 U.S.C. § 1402(a)(13) and 42 U.S.C. § 411(a)(12). This exception generally excludes the distributive share of income or loss of a limited partner from net earnings from self-employment, with a specific carveout for "guaranteed payments . . . for services actually rendered". Denham contends that the Tax Court erred by distorting the meaning of "limited partner" through the imposition of a "functional analysis test" and by inappropriately allowing this partner-level determination to occur in a partnership-level proceeding under the TEFRA regime.

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IRS Announces Policy for the One Big Beautiful Bill Act for 2025 Payroll Issues

The Internal Revenue Service (IRS) recently issued a significant announcement, IR-2025-82, on August 7, 2025, detailing its phased implementation strategy for the One Big Beautiful Bill Act (OBBBA). This news release provides crucial clarity for tax professionals regarding individual information returns and federal income tax withholding for Tax Year (TY) 2025, while also offering a glimpse into forthcoming changes for TY 2026.

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Proactive Engagement with the Office of Professional Responsibility

The Internal Revenue Service’s Office of Professional Responsibility (OPR) recently issued an OPR Alert, "Fessing Up Can Be in Your Own Best Interests: Self-Reporting of Practitioner Misconduct," on August 6, 2025. This communication offers crucial insights for Certified Public Accountants (CPAs) and Enrolled Agents (EAs) who practice before the IRS, emphasizing the framework of Circular 230 and the potential advantages of proactive self-reporting of misconduct. As tax professionals, understanding these dynamics is paramount to maintaining our privilege of practice and managing potential disciplinary actions effectively.

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Understanding Passthrough Losses and Bankruptcy in Field Attorney Advice 20253101F

Field Attorney Advice (FAA) 20253101F, released on August 1, 2025, addresses two critical issues concerning a net operating loss (NOL) carryback claimed by individual taxpayers who are shareholders of an S corporation undergoing Chapter 7 bankruptcy. This memorandum provides valuable insight into the application of S corporation passthrough rules and the implications of corporate bankruptcy on shareholder tax attributes.

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Proposed Amendments to IRC Section 132 Fringe Benefit Rules: Switching to NAICS

The Department of the Treasury and the Internal Revenue Service (IRS) have issued proposed regulations (REG-132805-17) concerning the determination of an employer’s line of business for purposes of applying the exclusion from gross income for no-additional-cost services and qualified employee discounts under Internal Revenue Code (IRC) Section 132. These proposed regulations are intended to update the business classification system used for these fringe benefits to better reflect current economic activity and reduce administrative burden.

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Closer This Time, But Still Not Quite There—Another Microcaptive Loss for the Taxpayers

The United States Tax Court recently rendered a significant decision in CFM Insurance, Inc. v. Commissioner, T.C. Memo. 2025-83, a case that adds another layer to the complex landscape of microcaptive insurance arrangements. This article provides a comprehensive overview of the case, from its foundational facts to the Tax Court’s nuanced legal analysis and ultimate conclusions.

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Post-Referral Authority in Tax Litigation—IRS Lacked Authority to Approve ERC Refund

The recent decision in JPM Restaurant, LLC v. United States, case No. 1:24-cv-00357, from the United States District Court for the Eastern District of Tennessee, offers important insights for tax professionals navigating Employee Retention Credit (ERC) claims that evolve into litigation. This case highlights critical jurisdictional boundaries regarding tax liability compromises once a matter is referred to the Department of Justice (DOJ).

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Urgent Guidance Requested on Section 174A Domestic Research and Experimental Expenditures

The American Institute of CPAs (AICPA) has formally requested immediate guidance from the Department of the Treasury and the Internal Revenue Service (IRS) regarding Section 174A of the Internal Revenue Code (IRC), which pertains to domestic research and experimental expenditures (domestic research costs). This urgent appeal, addressed to the Honorable Kenneth J. Kies, Assistant Secretary of the Treasury, Tax Policy, highlights critical issues facing eligible small business taxpayers as they finalize their 2024 federal income tax returns.

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Innocent Spouse Relief and the Doctrine of Constitutional Avoidance

The recent decision by the United States Court of Appeals for the Eleventh Circuit in Fannie Wright v. Commissioner of Internal Revenue, No. 24-10563, offers important insights into innocent spouse relief and the application of constitutional law in tax disputes. This article details the factual background, the taxpayer’s request for relief, and the Eleventh Circuit’s rigorous analysis of the law, its application to the facts, and the conclusions reached.

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Microcaptive Arrangements Under Scrutiny Yet Again

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.

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Defining Educational Organizations for UBIT Purposes

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.

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Interest Netting Post-Merger: The “Same Taxpayer” Requirement

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.

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Streamlining Corporate Alternative Minimum Tax for Partnership Investments: An Examination of Notice 2025-28

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.

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IRS Commissioner Predicts the Upcoming Filing Season Will Begin Around President’s Day

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.

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Tax Court Scrutiny of Settlement Income and Business Deductions: A Case Study from Mennemeyer v. Commissioner

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.

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Changes to Tax Examinations: IRS LB&I’s Updated Directives

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.

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Employer Shared Responsibility Payments: Updates for 2026 and Core Provisions

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.

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Filing Proper Refund Claims: A Cautionary Tale for Tax Professionals

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.

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Substantiating Noncash Charitable Contributions: A Review of Besaw v. Commissioner

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.

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