Introduction
On September 4, 2026, the U.S. Department of the Treasury (“Treasury”) and the Internal Revenue Service (the “IRS”) published proposed regulations (the “Proposed Regulations”) that would revoke the tax-exempt status of a private school if it adopts, maintains, or enforces a policy or practice that discriminates on the basis
Introduction
On August 14, 2026, the Maryland Tax Court struck down the state’s Digital Advertising Gross Revenues Tax (the “Tax”). In Apple Inc. v. Comptroller, Google LLC v. Comptroller and Peacock TV, LLC v. Comptroller, the court held that the Tax violated the federal Internet Taxation Freedom Act
On August 12, 2026, in K Alain, L.L.L.P. v. Commissioner,[1] the U.S. Court of Appeals for the Fifth Circuit withdrew its taxpayer-friendly January 16, 2026 opinion in Sirius Solutions, L.L.L.P. v. Commissioner,[2] and replaced it with a decision that is ambiguous in its application but appears
On May 5, 2026, the Internal Revenue Service (“IRS”) released Revenue Procedure 2026-21 (the “Rev. Proc.”), which reinstates a program under which taxpayers may request private letter rulings (“PLRs”) on “significant issues” arising in certain corporate transactions[1] without asking the IRS to rule on the entire integrated transaction.[2]
On April 21, 2026, in Liberty Global, Inc. v. United States, the Tenth Circuit held that the economic substance doctrine was “relevant” and applied to deny Liberty Global, Inc. a $2.4 billion deduction and imposed a 40% penalty with respect to a transaction known as “Project Soy”. The Tenth
Update: The National Taxpayer Advocate has published a blog post urging taxpayers to evaluate whether they have claims for refund based on the recent Abdo and Kwong decisions. Importantly, the Taxpayer Advocate suggests that the argument for penalty and interest relief based on the COVID pandemic disaster declarations is
On March 19, 2026, in Jones Bluff, LLC v. Commissioner, 166 T.C. No. 6 (2026), the Tax Court held that a partnership could not assert due process claims to invalidate an IRS adjustment on behalf of its partners under the Bipartisan Budget Act of 2015 (the “BBA”) regime. The
Although many of the procedural rules for auditing partnerships at the federal level have changed under the Bipartisan Budget Act of 2015 (the “BBA”), some principles—like the effect of actual notice—remain the same. Under the BBA, the IRS proposes partnership-level adjustments in a Notice of Proposed Partnership Adjustment (“NOPPA”) and later finalizes them in a Notice of Final Partnership Adjustment (“FPA”). If the IRS issues the FPA after the statute of limitations expires, the partnership can seek to invalidate it as untimely.
A reviewed Tax Court opinion filed March 9, 2026—Mammoth Cave Property, LLC v. Commissioner, No. 5401-24, 166 T.C. No. 4—shows the limits of “defective notice” arguments when the partnership actually received the NOPPA and participated in the process.
Relief from underpayment interest, failure-to-file penalties, and failure-to-pay penalties—as well as relief from IRS filing deadlines that arose during the COVID-19 pandemic—may be possible under two recent federal cases from the US Tax Court and the US Court of Federal Claims. Specifically, the recent Kwong decision indicates that the period of the COVID-19 federally declared disaster extended from January 20, 2020 to July 10, 2023. Filing deadlines that would have normally occurred and interest and penalties that would have normally accrued during this period may have been suspended under the reasoning articulated in Kwong. Taxpayer deadlines for seeking relief are fast approaching, and the time to review pandemic-era tax filings and tax accounts is now.
On February 10, 2026, Judge Jed Rakoff of the Southern District of New York ruled in United States v. Heppner that documents generated through a consumer version of Anthropic’s Claude AI were not protected by the attorney-client privilege or the work-product doctrine under the circumstances presented. The decision appears to be the first to squarely address privilege and work product claims arising from a non-lawyer’s use of a consumer-grade insecure, non-enterprise AI tool for “legal research,” as well as the potential consequences of inputting privileged information (provided to an individual by counsel) into an AI tool. However, putting the novelty of the AI context aside, Judge Rakoff grounded his analysis in traditional privilege principles: that disclosure of privileged communications to a third party in circumstances that undermine confidentiality (here, the corporation operating the AI tool) may result in waiver. And that an AI tool is just that – a tool, not an attorney. Accordingly, this decision reinforces the importance of only using properly secured AI tools with confidential or privileged information and for decisions about using AI in the privileged context to be made by those who best appreciate the risks involved: i.e., lawyers.