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Supreme Court hears case on insurance and estate taxes

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In its second case this term involving tax policies affecting financial advisors’ clients, the Supreme Court will decide a complex question about life insurance and the value of an estate.

Connelly v. Internal Revenue Service reached arguments March 27 at the high court, where justices struggled to grasp the complications around the impact on the value of a company for purposes of the estate tax from life insurance proceeds tied to the death of a shareholder. 

The petitioner, Connelly, argued that the IRS should not include the proceeds of the redemption of a family-owned company’s policy on his brother’s life in their construction firm’s value because that insurance money immediately bought the remaining shares. The IRS collected additional tax of $889,914 from the deceased brother’s estate based on the agency’s view that the proceeds boosted the company’s value. Two lower courts ruled in favor of the IRS.

Most observers noticed skepticism among the justices for the business owner’s stance that the IRS overvalued the company, although many people would likely agree with Justice Brett Kavanaugh’s observation at the hearing that some concepts in the case are “extremely difficult.” The session came a few months after arguments in Moore v. U.S. about a provision of the 2017 Tax Cuts and Jobs Act in a case amounting to a major challenge to government taxing power

In theory, many tax experts could see how including the insurance proceeds in the company’s valuation “rises to the level of being unfair” to an estate when the policy requires them to be redeemed by purchasing the deceased family members’ shares, said Jose Reynoso, the head of personal financial planning and advance estate and tax for Citizens Private Wealth.

“It’s really interesting to us as planners and practitioners that the Supreme Court even took it up,” Reynoso said in an interview. “It’s a unique, sort of nichey thing that impacts not too many people.”

READ MORE: A tax on ‘unrealized’ income? A test for wealth laws at the Supreme Court

The issue does come up frequently for the owners of closely held businesses who purchase life insurance policies for their largest shareholders, he noted. The IRS valuation of the construction company “would destroy a valuable succession planning tool that the nation’s small businesses have openly used for decades,” the plaintiff’s attorney, Kannon Shanmugam, said at the hearing, according to the transcript

The U.S. Chamber of Commerce and the National Federation of Independent Business Small Business Legal Center submitted a brief in support of that position. Still, justices from both the conservative and liberal sides of the court kept asking Shanmugam about the effect on prospective buyers’ offers for the company from about $3 million in insurance proceeds flowing to the surviving brother, the SCOTUSblog reported.

Their apparent siding with the IRS and “tepid reception to the taxpayer estate” was not “entirely surprising” to Frank Paolini, partner with the private wealth services group at the Neal Gerber Eisenberg law firm. 

“While I could make arguments on either side of the case, the taxpayer estate must still contend with the logically glaring issue that a policy covering the life of a key shareholder would have an impact on the fair market value of the shares in any other context,” Paolini said in an email. 

“For instance, a hypothetical buyer of the company would ascribe additional value to the shares if the company held a policy on the life of key employees and shareholders,” he continued. “Just because the company must use the policy proceeds to pay the decedent’s family for the shares, the shares are still redeemed, and the value of the purchased equity is returned to the company on redemption,” he said.

“Essentially, the value of the shares must go somewhere when the decedent dies. In the end, the family receives the benefit of the payment from the policy and the company receives the shares back in return, which is presumably equal to the value of the shares purchased from the decedent’s estate. If the court held otherwise, it would seem incongruent with many other areas of estate tax valuation,” Paolini said.

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The plaintiffs held that the government was taking positions that are out of step with the fact that the surviving brother would still be subject to capital gains taxes and rulings in other cases that contradicted the use of the proceeds in a valuation. However, their argument revolved around the notion that “before you can value something, you must first subtract the price paid for the very thing you are trying to value,” U.S. Department of Justice Assistant to the Solicitor General Yaira Dubin told the court.

“A redemption obligation divides the corporate pie among existing shareholders without changing the value of their interests,” Dubin said. “And, here, the corporate pie was worth $6.86 million, not $3.86 million.” 

Just as in the Moore case, the Supreme Court took up a matter that could reap massive changes to clients’ tax bills, then displayed some reluctance toward such drastic shifts. Regardless, the justices again discussed topics that clients could raise with their advisors and other tax professionals and even touched on potential planning methods. 

Toward the end of the 54-minute hearing last month, Dubin spoke with the justices about how a cross-insurance agreement between the brothers or a trust structure could enable the taxpayers to avoid having the proceeds go into their corporation’s valuation. The Supreme Court will release decisions in the Moore and Connelly cases by the end of June or early July. 

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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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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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