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Supreme Court ruling on life insurance proceeds has estate tax implications

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In a landmark decision earlier this year, the Supreme Court addressed a crucial issue regarding the valuation of shares in closely held corporations for federal estate tax purposes.

The case, Connelly v. United States (2024), clarified whether life insurance proceeds that are used to redeem a deceased shareholder’s stock should be factored into the stock’s valuation for estate tax calculations. The decision has many implications for CPAs, tax professionals, estate planners and investment advisors.

Case overview

Michael and Thomas Connelly were the sole shareholders of Crown C Supply, a closely held building supply corporation. To ensure continuity and to retain ownership within the family, they had a stock redemption agreement funded by corporate-owned life insurance policies worth $3.5 million each. ‘

Upon Michael’s death, the corporation used $3 million from the life insurance proceeds to redeem his shares. But the IRS and the Connelly estate couldn’t agree on the proper valuation of Michael’s shares. The estate valued the shares based on the $3 million redemption payment, but the agency insisted that the life insurance proceeds should be included in the company’s valuation. From the IRS perspective, the proceeds  would raise the total value of the estate to $6.86 million, consequently valuing Michael’s shares at $5.3 million.

This valuation led to a significant additional estate tax liability for the Connelly estate.

Supreme Court decision

The Supreme Court sided with the IRS, affirming that life insurance proceeds should be included in the corporation’s value when determining the value of the decedent’s shares. The court clarified that the obligation to redeem shares at fair market value is not a liability that reduces the corporation’s value for estate tax purposes.

The court’s decision means that the life insurance proceeds used for the redemption would increase the corporation’s total value, thereby increasing the value of the shares held by the deceased at the time of death.

Contradiction in Blount v. Commissioner

The Connelly decision brings to mind the precedent set in Blount v. Commissioner (2005) two decades earlier. In Blount, the Eleventh Circuit concluded that life insurance proceeds should be excluded (not included) from the valuation of a corporation when they are used to fund a stock redemption obligation.

As you can see, the Supreme Court’s recent Connelly decision rejected the Eleventh Circuit’s approach, finding it “demonstrably erroneous.” Again, the Supreme Court emphasized that a redemption obligation does not offset the value of the life insurance proceeds and should be included in the corporation’s value for estate tax purposes.

This divergence highlights the Supreme Court’s intent to provide a clear and unified approach to handling such cases.

Implications for estate planning

This Connelly ruling underscores the importance of strategic planning for closely held businesses to avoid unexpected tax liabilities. Here are three strategies to consider:

1. Cross-purchase agreements. By using a cross-purchase agreement instead of a corporate redemption agreement, the surviving shareholders individually purchase life insurance policies on each other. Upon a shareholder’s death, the surviving shareholders use the proceeds to buy the decedent’s shares directly. This method ensures that the life insurance proceeds do not inflate the corporation’s value for estate tax purposes, since the proceeds are not part of the corporate assets.

Advantages of cross-purchase agreements:

  • Tax efficiency: The insurance proceeds do not increase the corporation’s value, avoiding higher estate taxes.
  • Direct ownership transfer: Shares are directly transferred to surviving shareholders, maintaining business continuity.
  • Flexible ownership structure: This allows for adjustments in ownership percentages without involving the corporation itself.

 Challenges and considerations:

  • Funding requirements: Ensuring adequate funding for the insurance premiums and potential buyouts can be challenging, especially for smaller businesses.
  • Regulatory compliance: The agreement must comply with relevant laws and regulations, which may require professional legal and financial advice.

2. Defensible valuation methods. To prevent disputes and to ensure compliance with tax laws, it is crucial to establish defensible valuation methods within buy-sell agreements. These methods can include binding appraisals conducted by qualified professionals, formula valuations, or regularly updated agreed values.

Best practices for establishing valuation methods:

  • Regular review: Regularly reviewing and updating buy-sell agreements ensures they reflect current business values and comply with evolving laws.
  • Professional appraisals: Using qualified professionals for appraisals can provide a more accurate and defensible valuation.

3. Legal and regulatory compliance. Ensure that buy-sell agreements meet the requirements of Section 2703 of the Internal Revenue Code governing acquisition or transfer of property at less than FMV. This section disregards valuations in buy-sell agreements unless they are bona fide arrangements, not devices to transfer property to family members for less than full and adequate consideration. They must be comparable to similar arrangements in arm’s-length transactions.

The Supreme Court’s decision in Connelly v. United States highlights the need for closely held businesses to reassess their estate planning and buy-sell agreements. By considering alternative strategies like cross-purchase agreements and by ensuring defensible valuation methods, businesses can better manage their estate tax liabilities and ensure smoother ownership transitions. 

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Accounting

Continuous Auditing Transforms Corporate ERPs

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continuous auditing transforms corporate erps

As corporate accounting departments cross the threshold into late July 2026, the adoption of continuous, automated auditing systems has reached a definitive turning point. Driven by advances in artificial intelligence and deep integration with modern Enterprise Resource Planning (ERP) platforms, leading finance organizations are moving away from traditional, periodic post-hoc audits in favor of real-time, 100% transactional verification. This technological transition is redefining internal control environments, reducing compliance costs, and eliminating the structural delays inherent in legacy quarterly closing processes.

Unlike traditional auditing frameworks that rely on statistical sampling—a process that inevitably leaves operational blind spots—continuous auditing software monitors operational data feeds continuously. Every purchase order, electronic invoice, payroll disbursement, and cross-border wire transfer is automatically cross-referenced against established corporate governance parameters, regulatory tax schedules, and anti-fraud algorithms in real time. Anomalies or unauthorized ledger entries are flagged instantly, allowing internal audit teams to investigate and remediate compliance gaps immediately rather than months after the close of a financial period.

The implications for executive financial management are far-reaching. By embedding continuous verification directly into daily transaction workflows, chief financial officers gain uninterrupted visibility into the organization’s true financial standing. Real-time balance sheet auditing eliminates the severe operational bottlenecks associated with month-end and quarter-end financial reconciliations, freeing accounting professionals to focus on strategic financial modeling, tax planning, and capital allocation rather than manual data entry and spreadsheet consolidation.

However, implementing continuous auditing requires accounting leadership to invest heavily in data governance and technical upskilling. Internal audit teams must evolve from manual ledger reviewers into system architects capable of auditing complex algorithms and validating automated data pipelines. Accounting firms and corporate controllers that master continuous auditing will establish a resilient compliance framework capable of meeting stringent international regulatory standards with total transparency.

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Accounting

U.S. Imposes New 50% Tariffs on Canadian Imports Under Rare Legal Provision

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U.S. Imposes New 50% Tariffs on Canadian Imports Under Rare Legal Provision

WASHINGTON — In a major escalation of cross-border trade friction, U.S. President Donald Trump has signed executive orders imposing new 50% tariffs on a wide selection of Canadian exports, citing discriminatory practices by Ottawa targeting American auto, dairy, and beverage industries.

The new duties, announced Monday, will take effect in 30 days. They target a broad spectrum of consumer and industrial goods—ranging from wine, liquor, and milk products to commercial cement, furniture, clothing, and hockey equipment.

Untested Legal Mechanism

To enact the sweeping measures, the administration invoked Section 338 of the Tariff Act of 1930—a rarely used legal provision allowing the executive branch to levy additional tariffs of up to 50% on foreign nations deemed to discriminate against U.S. commerce.

White House officials noted that Section 338 addresses trade discrimination rather than national security or economic emergencies. The move comes months after prior global emergency tariffs faced legal challenges in domestic courts, signaling Washington’s pivot toward alternate statutory authorities to maintain import duties.

Senior administration officials briefed reporters that the measure directly responds to Canadian provincial bans on U.S. alcohol, restrictions on American vehicle exports, and import quota disparities affecting U.S. dairy and cheese producers relative to third-party trading partners.

“While the administration continues to secure reciprocal trade agreements globally, Canada retaliated against efforts to protect domestic industry,” U.S. Trade Representative Jamieson Greer stated.

USMCA Impact and Carve-Outs

Significantly, the newly ordered 50% duties will apply to designated items even if they otherwise comply with the United States-Mexico-Canada Agreement (USMCA).

However, the administration confirmed key targeted exemptions:

  • Energy products (including oil and natural gas)
  • Potash and critical minerals
  • Fish and seafood
  • Goods already governed by sector-specific duties (such as existing steel and aluminum tariffs)

Administration representatives emphasized that the tariffs do not stem from recent disputes concerning drifting Canadian wildfire smoke, noting that policy options regarding environmental spillover remain under separate review.

Canadian Response and Market Reaction

Following the White House announcement, the Canadian dollar experienced a sharp decline against the U.S. dollar, falling approximately 0.4% during evening trading.

Canadian Prime Minister Mark Carney issued a statement emphasizing that Canada’s earlier counter-duties had merely matched previous U.S. trade actions. “Canada stands ready to engage intensively to address outstanding issues with the U.S. to the mutual benefit of our citizens,” Carney stated, pointing to detailed proposals Ottawa submitted to modernize the USMCA framework.

Ontario Premier Doug Ford took a firmer stance, urging a “dollar-for-dollar” reciprocal response if the measures go into effect on August 19.

With a 30-day implementation window before the duties officially lock in, industry associations and trade groups on both sides of the border are calling for urgent bilateral negotiations to avert further supply chain disruption across North America.

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Accounting

Automated Continuous Auditing: Transforming Compliance and Real-Time Financial Oversight

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Transforming Compliance and Real-Time Financial Oversight

The traditional accounting paradigm—defined by periodic monthly closures and post-hoc annual audits—is rapidly giving way to continuous, automated financial oversight. As of July 2026, forward-thinking accounting practices and multinational corporate finance departments are leveraging continuous auditing systems powered by advanced machine learning models. These systems monitor operational transactions in real time, shifting audit methodologies from sample-based post-analysis to absolute, 100% transaction-level verification.

The operational advantages of continuous auditing are transformative. Standard auditing procedures historically relied on statistical sampling, which, despite rigorous methodology, inherently left gaps where anomalies or fraudulent transactions could go undetected for months. Modern continuous auditing platforms integrate directly with enterprise resource planning (ERP) databases, instantly cross-referencing purchase orders, invoices, bank feeds, and tax records. Any deviation from established control parameters or unusual transaction behavior triggers immediate flags for internal audit teams, dramatically reducing detection lag from quarters to seconds.

Beyond fraud prevention, continuous auditing fundamentally alters internal reporting and decision-making. Executive leadership no longer has to wait weeks after the close of a quarter to evaluate precise financial standing; real-time verified ledger data provides an uninterrupted view of operating margins, tax liabilities, and cash flow dynamics. This real-time visibility enables corporate controllers to adjust capital allocation strategies dynamically, mitigating liquidity constraints and capitalizing on emerging commercial opportunities far more efficiently than competitors bound to legacy reporting cycles.

However, implementing continuous auditing requires accounting professionals to acquire new analytical capabilities. The role of the auditor is evolving from manual data reconciliation toward system validation, algorithmic model governance, and strategic risk interpretation. Accounting firms and corporate finance departments must invest in continuous technical education, ensuring that audit staff possess the data engineering skills necessary to design, maintain, and evaluate complex automated compliance systems.

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