The Department of the Treasury and the Internal Revenue Service (IRS) have issued proposed regulations (REG-112829-25) addressing backup withholding obligations for Third Party Settlement Organizations (TPSOs). These proposals are designed to harmonize the backup withholding regulations under Internal Revenue Code (IRC) section 3406 with the recent statutory amendments to IRC section 6050W enacted by the "One, Big, Beautiful Bill Act" (OBBBA).

For tax professionals advising TPSOs or participating payees, these proposed regulations represent a significant technical shift from the existing regulatory framework. Specifically, they modify the determination of "reportable payments" subject to backup withholding by incorporating the de minimis thresholds found in section 6050W(e).

In a decision solidifying the judicial consensus regarding civil penalties under the Bank Secrecy Act (BSA), the United States Court of Appeals for the Second Circuit recently affirmed a summary judgment ruling in United States v. Reyes. The court held that the statutory term "willfully" encompasses reckless conduct for purposes of imposing enhanced civil penalties for failing to file a Report of Foreign Bank and Financial Accounts (FBAR). Furthermore, the court confirmed that the six percent late payment penalty assessed by the Treasury Department is mandatory, leaving district courts with no discretion to reduce it.

For tax professionals representing clients with significant noncash charitable contributions, the statutory and regulatory substantiation hurdles remain high. A recent decision by the United States Tax Court, Gibson v. Commissioner, T.C. Summary Opinion 2026-1, serves as a stark reminder of the consequences of failing to strictly comply with Internal Revenue Code (I.R.C.) section 170(f)(11) and the associated Treasury Regulations. Although summary opinions are not binding precedent, the Gibson case offers a textbook illustration of how the Court applies the tiered substantiation requirements to high-value property donations.

The United States Tax Court recently issued a Memorandum Opinion in Milk Saving Starving Children Foundation v. Commissioner, T.C. Memo. 2026-1, which serves as a stark reminder regarding the operational test under Internal Revenue Code (I.R.C.) section 501(c)(3). The Court granted the Commissioner’s Motion for Summary Judgment, sustaining the revocation of the petitioner’s tax-exempt status due to its failure to operate exclusively for exempt purposes. This article details the factual background, the legal framework applied by Special Trial Judge Leyden, and the specific operational failures that led to the adverse determination.

The Department of the Treasury and the Internal Revenue Service (IRS) have issued Notice of Proposed Rulemaking REG-113515-25, providing guidance on the newly enacted deduction for Qualified Passenger Vehicle Loan Interest (QPVLI). These proposed regulations interpret amendments made to the Internal Revenue Code (Code) by the "One, Big, Beautiful Bill Act" (OBBBA), Public Law 119-21.

In Barney v. Commissioner, T.C. Memo. 2025-133, the United States Tax Court addressed complex issues surrounding the conversion of for-profit entities into nonprofit organizations via a bargain sale. The case serves as a critical study for tax professionals regarding the valuation of distressed assets, the substantiation requirements for charitable contributions under Internal Revenue Code section 170, and the calculation of the amount realized under section 1001 when consideration takes the form of promissory notes.

In the recent Tax Court Memorandum decision Estate of Spenlinhauer v. Commissioner, T.C. Memo. 2025-134, the Court addressed a complex mix of procedural failures, valuation disputes, and phantom assets. For tax professionals, this case serves as a stark reminder of the cascading consequences of failing to timely file Form 706, the strict substantiation requirements for Section 2053 deductions, and the piercing nature of transferee liability under Section 6901.

The Internal Revenue Service has issued its annual guidance regarding the procedures for issuing letter rulings, determination letters, and technical advice. For the 2026 cycle, practitioners must familiarize themselves with Revenue Procedure 2026-1, Revenue Procedure 2026-2, Revenue Procedure 2026-3, Revenue Procedure 2026-4, and Revenue Procedure 2026-5. These documents collectively establish the administrative framework for tax administration, delineating the jurisdiction of Associate Chief Counsel offices, the rights of taxpayers during examination and appeals, and the specific areas where the Service will decline to issue private guidance. The following analysis details the legal basis for these procedures and highlights the significant changes affecting tax practice for the upcoming year.

The Internal Revenue Service has issued Notice 2026-10, establishing the optional standard mileage rates for computing the deductible costs of operating an automobile for business, charitable, medical, or moving expense purposes effective January 1, 2026. This guidance also updates the basis reduction amounts for depreciation and sets the maximum standard automobile cost for fixed and variable rate (FAVR) plans.

On December 23, 2025, the Internal Revenue Service released updated guidance in Fact Sheet FS-2025-10, titled "Updates to Questions and Answers about the Premium Tax Credit." This issuance supersedes previous guidance and incorporates critical legislative changes enacted under P.L. 119-21, specifically regarding the expiration of temporary relief measures codified in Internal Revenue Code (IRC) Section 36B. For tax professionals, the most immediate and material technical updates concern the sunsetting of repayment limitations for excess Advance Premium Tax Credits (APTC) and the adjustment of applicable affordability percentages for tax years beginning after December 31, 2025.

The Internal Revenue Service recently released Fact Sheet 2025-09 (FS-2025-09), providing updated guidance on the limitation on business interest expense deductions under Internal Revenue Code Section 163(j). This guidance incorporates significant statutory amendments arising from the legislation referred to as the "One, Big, Beautiful Bill" (P.L. 119-21). For tax professionals, these updates necessitate a careful review of adjusted taxable income (ATI) computations, the definition of motor vehicles for floor plan financing, and the interaction between interest limitations and capitalization rules.

This article examines the December 2025 revised questions within the Fact Sheet, correlating the IRS’s administrative positions with the underlying statutory text of Section 163(j). Note that while the prompt requests conclusions from a "court" or "judge," the provided source material consists of administrative guidance and statutory code; therefore, the analysis focuses on the conclusions and determinations issued by the IRS and Congress.

The following are detailed descriptions of the top 10 tax crime cases of 2025 as identified by the IRS Criminal Investigation (IRS-CI) Division. These cases involve a range of financial crimes including pandemic relief fraud, public corruption, cybercrime, and tax evasion.

The recent enactment of the One, Big, Beautiful Bill Act (OBBBA) introduced significant changes to the Internal Revenue Code, specifically regarding the sale of agricultural assets. One of the most critical additions for our clients in the agricultural sector is the new Internal Revenue Code (IRC) Section 1062. This section allows for the deferral of tax liability arising from specific farmland dispositions. However, the interaction between this deferral mechanism and the estimated tax payment requirements under IRC Sections 6654 and 6655 created an immediate technical conflict.

To resolve this, the Internal Revenue Service released Notice 2026-3. This article examines the statutory framework of the Section 1062 election, the estimated tax conflict it created, and the specific relief provided by the Notice.

The Department of the Treasury and the Internal Revenue Service have issued Notice 2026-6, granting additional transition relief regarding the administration of State paid family and medical leave (PFML) programs. This guidance extends the non-enforcement period originally established in Revenue Ruling 2025-4, specifically concerning the taxation and reporting of medical leave benefits attributable to employer contributions.

For practitioners advising state administrators or employers participating in state PFML initiatives, it is critical to distinguish between the relief that has been extended and the specific compliance requirements that will nonetheless take effect in 2026.

A significant development in federal drug policy occurred on December 18, 2025, with the issuance of a new Executive Order prioritizing the rescheduling of marijuana. For CPAs with clients in the state-legal cannabis sector, this action signals a potential and expeditious end to the onerous tax burdens imposed by Internal Revenue Code (IRC) Section 280E.

This article details the new Executive Order, reviews the proposed rule it addresses, and analyzes the technical tax implications regarding Schedule I status and the deductibility of business expenses.

In the recent Tax Court Memorandum decision Fussell v. Commissioner, T.C. Memo. 2025-131, the Tax Court offered a stark reminder regarding the stringent substantiation requirements for business bad debts under Internal Revenue Code (IRC) Section 166 and the mechanical application of Net Operating Loss (NOL) carryovers under Section 172. For tax professionals, this case serves as a critical case study on the distinction between capital contributions and bona fide debt, as well as the burden of proof required to sustain NOL deductions in years subsequent to the alleged loss.

For tax practitioners representing cannabis clients, the intersection of I.R.C. § 280E and collection alternatives has long been a contentious battlefield. On December 16, 2025, the United States Tax Court issued two opinions regarding Mission Organic Center, Inc.—a reviewed opinion covering tax years 2016 through 2020, and a memorandum opinion covering tax year 2021.

These decisions provide critical guidance on how the Internal Revenue Service (IRS) calculates Reasonable Collection Potential (RCP) for marijuana businesses and underscores the procedural requirements Settlement Officers must follow to avoid an abuse of discretion. While the Tax Court upheld the Service’s harsh policy of disregarding § 280E-disallowed expenses when calculating RCP in the reviewed opinion, it simultaneously remanded the 2021 case due to the Appeals Officer’s failure to properly review the administrative record.

In the wake of the Supreme Court’s decision in SEC v. Jarkesy, 144 S. Ct. 2117 (2024), tax practitioners have closely monitored how the judiciary would apply the Seventh Amendment’s jury trial requirement to Internal Revenue Service (IRS) penalty assessments. In Riddle Aggregates, LLC v. Commissioner, 165 T.C. No. 12 (Dec. 15, 2025), the Tax Court addressed this issue head-on regarding accuracy-related penalties asserted in a partnership-level proceeding.

This article details the facts, the constitutional arguments raised by the petitioner, and the Tax Court’s technical analysis rejecting the applicability of the Seventh Amendment to civil tax penalties under I.R.C. § 6662.

For tax professionals representing clients with commingled funds and unfiled returns, the recent Tax Court decision in Chernomordikov v. Commissioner, T.C. Memo. 2025-129, offers a critical examination of the bank deposits method, the substantiation of Cost of Goods Sold (COGS), and the high evidentiary bar required to sustain fraudulent failure to file penalties. While the court sustained the majority of the deficiencies based on the taxpayer’s lack of records, the decision regarding the fraud penalty provides a nuanced look at how the "missing witness" rule applies when a tax preparer fails to testify.

With the enactment of the "One, Big, Beautiful Bill Act" (Public Law 119-21) in July 2025, Congress introduced a new nonrefundable income tax credit under Internal Revenue Code Section 25F. This credit, effective for calendar years beginning in 2027, incentivizes qualified contributions to Scholarship Granting Organizations (SGOs). To facilitate the implementation of this credit, the Internal Revenue Service released Revenue Procedure 2026-6. This article examines the procedural framework established by the IRS, detailing the statutory background, the mechanism for State elections, and the specific requirements for the "Advance Election" process.