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IRS activity, documentation standards, and positions built to withstand scrutiny.

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Tax AlertMay 20266 min read

IRS Conservation Easement Settlement: 90-Day Window, 10% Penalty — Then Terms Worsen

On May 13, 2026, the IRS announced IR-2026-65, a time-limited settlement initiative for more than 1,100 syndicated conservation easement disputes — roughly 740 docketed in Tax Court and 400 still in examination. Eligible taxpayers who accept within an initial 90-day window concede the charitable contribution deduction (recovering only an "other deduction" for approximate out-of-pocket costs) and pay a 10% gross valuation misstatement penalty under § 6662(h); that penalty rises to 20% in a subsequent, final 45-day window, with no extensions. Decline, and the case reverts to a hazards-of-litigation posture against a record in which courts have allowed, on average, about 6% of the claimed deduction and generally imposed 40% penalties.

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AnalysisMay 20264 min read

An ERC Disallowance Starts a Two-Year Clock — and the IRS Just Built a Pressure Valve

A denied Employee Retention Credit claim is not the end of the matter, but it does start a clock: a taxpayer generally has two years from the disallowance letter to resolve the claim or sue for the refund. In April 2026, the IRS introduced a process — Notice CP320B and Form 907 — to extend that deadline for taxpayers still waiting on the agency to review their response. For businesses with claims caught in the backlog, this is the difference between preserving the right to sue and losing it.

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AnalysisApril 20265 min read

The IRS Is Withdrawing Its Partnership Basis-Shifting Rules — Read the Tempo, Not Just the Headline

In March 2026, Treasury proposed to remove the reporting regulations that, a year earlier, had branded certain related-party partnership basis adjustments as "transactions of interest." Combined with a sharply smaller IRS workforce, the move reads like a retreat from partnership enforcement. It is a real reduction in disclosure exposure — but it is not a signal that aggressive structures have become safe. The substantive law has not changed, and the cases still in litigation are being decided for the government.

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AnalysisApril 20269 min read

After *Liberty Global*: Technical Code Compliance No Longer Shields a Transaction From the Economic Substance Doctrine

On April 21, 2026, a divided Tenth Circuit affirmed the disallowance of an approximately $2.4 billion Section 245A dividends-received deduction in *Liberty Global, Inc. v. United States*, No. 23-1410, holding that the codified economic substance doctrine of Section 7701(o) reaches a tax-motivated, integrated transaction even when each step mechanically complies with Title 26. The decision is now the leading appellate authority on Section 7701(o), and it confirms that ordinary M&A building blocks — Section 351 contributions, entity-classification elections, intercompany reorganizations — are not categorically exempt when embedded in a plan that exploits a result Congress did not intend. Because Section 6662(b)(6) attaches a strict-liability accuracy penalty to economic-substance disallowances with no reasonable-cause escape, the planning and documentation stakes for sophisticated structures have risen materially.

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AnalysisApril 20255 min read

Congress Kills the DeFi Broker Rule: What Survives for 1099-DA Reporting

On April 10, 2025, the President signed H.J. Res. 25, nullifying the IRS rule that would have treated decentralized-finance front ends as brokers. The repeal was real and consequential — but it was also narrow. The separate, earlier rule requiring custodial brokers to issue Form 1099-DA for 2025 digital-asset sales was untouched. The reporting era did not end. It got smaller, and clearer.

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AnalysisFebruary 20256 min read

The Corporate Transparency Act in Limbo: What the Supreme Court's Stay Actually Changes

On January 23, 2025, the Supreme Court stayed one of the injunctions blocking the Corporate Transparency Act. The headlines read as if reporting was back on. It is not. A separate nationwide order still suspends the filing requirement, and FinCEN itself has said companies are not currently required to file. The defensible posture for closely held businesses is narrow and specific: prepare now, file nothing yet, and watch the second case.

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AnalysisDecember 20244 min read

Nationwide Whiplash: The CTA Injunction Saga Closes 2024 in Limbo

In the span of a few weeks, beneficial ownership reporting under the Corporate Transparency Act was frozen nationwide by a Texas court, reinstated by the Fifth Circuit, and frozen again by a different Fifth Circuit panel — all as the January 1 deadline for millions of companies bore down. As the year ends, the requirement is suspended, but precariously, and the litigation is unresolved. The only defensible posture is to be ready to file the moment the courts say so.

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AnalysisSeptember 20244 min read

The IRS Targets Partnership Basis Shifting: New Disclosure Rules and Economic-Substance Risk

The IRS has opened a coordinated campaign against a category of related-party partnership transactions it views as basis shifting without substance. The June 2024 guidance package does two things at once: it proposes to make these transactions reportable, and it signals that the economic-substance doctrine — and its strict-liability penalty — is in play. Partnerships and related-party structures that have used these techniques, or are contemplating them, need to review their exposure now.

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AnalysisAugust 20244 min read

The 1099-DA Era Is Real: Final Crypto Broker Reporting Rules for Custodial Platforms

Treasury has finalized the rules requiring custodial digital-asset brokers to report customer transactions on a new Form 1099-DA. The reporting starts with sales in 2025, which means the compliance build has to happen now. Centralized exchanges and other custodial platforms are squarely covered. Non-custodial and decentralized actors got more time — but they should read this as a deferral, not an exemption.

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AnalysisJuly 20244 min read

Chevron Is Gone: What Loper Bright Means for Challenging Treasury Regulations

The Supreme Court has overruled *Chevron*, the forty-year-old doctrine that told courts to defer to an agency's reasonable reading of an ambiguous statute. Courts must now interpret statutes themselves. For tax, this is not an abstract administrative-law event. It changes the odds in every dispute that turns on whether a Treasury regulation is a fair reading of the Internal Revenue Code — and it should change how taxpayers and the IRS alike approach contested positions.

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AnalysisMarch 20244 min read

The CTA's First Crack: Why a Favorable Ruling Does Not Suspend Your Filing Obligation

A federal court has held the Corporate Transparency Act unconstitutional. That is a real development, and it matters. But for the overwhelming majority of reporting companies, it changes nothing operational: the obligation to file beneficial ownership information with FinCEN remains in force. The mistake to avoid this quarter is reading a single district-court win as permission to stop.

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AnalysisDecember 20225 min read

After *Green Valley*, IRS "Listing" Notices Are on Shaky Ground: The APA Catches Up to Tax Guidance

The Tax Court's November 2022 decision in *Green Valley Investors, LLC v. Commissioner* set aside IRS Notice 2017-10 — which had designated certain conservation easements as listed transactions — on the ground that the Notice was a legislative rule that required notice-and-comment rulemaking under the Administrative Procedure Act. The decision accelerates a broader challenge to IRS sub-regulatory guidance across multiple areas, and its implications extend well beyond conservation easements.

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AnalysisDecember 20225 min read

The 2022 Domestic Filing Exception for K-2/K-3: A Narrow Door With a Partner-Notification Trap

For the 2022 tax year, the IRS formalized a domestic filing exception to the Schedules K-2 and K-3 requirements in revised instructions issued in October and December 2022. The exception is real and applies to a meaningful subset of domestic-only partnerships and S corporations. But the conditions that must be satisfied — including a partner-notification process — are more demanding than the exception's description suggests, and the penalty for inadvertently failing a condition is an obligation to file the schedules after the fact.

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AnalysisOctober 20224 min read

The IRS Just Named ERC Mills a Problem: Why Your Refund May Become a Liability

The IRS issued a direct public warning in October 2022 about aggressive Employee Retention Credit promoters — firms that are marketing the credit without performing eligibility analysis. For businesses that have claimed or are considering claiming the ERC based on a promoter's assurances, the warning signals that the burden of eligibility proof rests entirely with the taxpayer, not the promoter who helped file.

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AnalysisDecember 20217 min read

The Infrastructure Act Ended the Q4 Employee Retention Credit Retroactively: What Employers Who Already Reduced Deposits Must Do

The Infrastructure Investment and Jobs Act, signed November 15, ended the Employee Retention Credit for the fourth quarter of 2021 — except for recovery startup businesses — and made the cutoff retroactive to October 1. Because the law arrived six weeks into the quarter, many employers had already reduced their payroll tax deposits in anticipation of a credit that is no longer available. The IRS has now provided a penalty-relief safe harbor in Notice 2021-65, but it has hard deadlines, and missing them turns an anticipated credit into a failure-to-deposit penalty.

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AnalysisNovember 20217 min read

The Infrastructure Act's New Digital-Asset Reporting Rules: Why Crypto Recordkeeping Is a Now-Problem Even Though the Forms Arrive in 2024

The Infrastructure Investment and Jobs Act, signed November 15, enacted the first comprehensive information-reporting regime for digital assets. It expands the definition of "broker," requires basis reporting on crypto, mandates transfer statements when assets move to outside wallets, and — most controversially — treats digital assets as "cash" for the $10,000 trade-or-business reporting rule. The reporting itself does not begin until 2024. But the statute is law now, the scope of who counts as a "broker" was left deliberately open, and the basis-tracking it will eventually demand starts with transactions in 2023. The recordkeeping work is a present obligation, not a future one.

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AnalysisMay 20217 min read

A Unanimous Supreme Court Opens the Courthouse Door: What CIC Services Means for Challenges to IRS Reporting Mandates

On May 17, a unanimous Supreme Court held in CIC Services, LLC v. IRS that the Anti-Injunction Act does not bar a pre-enforcement lawsuit challenging an IRS reporting requirement, even though violating that requirement can trigger a tax penalty. The decision is narrow in what it resolves — it is about access to court, not the validity of any particular rule — but its consequence is broad. Taxpayers and advisors can now challenge IRS reporting and disclosure mandates issued without notice-and-comment before they comply, rather than being forced to break the rule or pay first and sue later.

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Tax AlertApril 20216 min read

The Filing Deadline Moved to May 17 — but First-Quarter Estimates Did Not

The IRS postponed the 2020 individual filing and payment deadline from April 15 to May 17. The relief is automatic and welcome, but it is also narrower than last year's, and the narrowness is the trap. First-quarter 2021 estimated tax payments stayed due April 15. So did C corporation returns and calendar-year trust and estate returns. A taxpayer who reads "deadline moved to May 17" as a blanket extension can miss a payment that the IRS deliberately left in place.

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