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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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New IRS regs put some partnership transactions under spotlight

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Final regulations now identify certain partnership related-party “basis shifting” transactions as “transactions of interest” subject to the rules for reportable transactions.

The final regs apply to related partners and partnerships that participated in the identified transactions through distributions of partnership property or the transfer of an interest in the partnership by a related partner to a related transferee. Affected taxpayers and their material advisors are subject to the disclosure requirements for reportable transactions. 

During the proposal process, the Treasury and the Internal Revenue Service received comments that the final regulations should avoid unnecessary burdens for small, family-run businesses, limit retroactive reporting, provide more time for reporting and differentiate publicly traded partnerships, among other suggested changes now reflected in the regs.

  • Increased dollar threshold for basis increase in a TOI. The threshold amount for a basis increase in a TOI has been increased from $5 million to $25 million for tax years before 2025 and $10 million for tax years after. 
  • Limited retroactive reporting for open tax years. Reporting has been limited for open tax years to those that fall within a six-year lookback window. The six-year lookback is the 72-month period before the first month of a taxpayer’s most recent tax year that began before the publication of the final regulations (slated for Jan. 14 in the Federal Register). Also, the threshold amount for a basis increase in a TOI during the six-year lookback is $25 million. 
  • Additional time for reporting. Taxpayers have an additional 90 days from the final regulation’s publication to file disclosure statements for TOIs in open tax years for which a return has already been filed and that fall within the six-year lookback. Material advisors have an additional 90 days to file their disclosure statements for tax statements made before the final regulations. 
  • Publicly traded partnerships. Because PTPs are typically owned by a large number of unrelated owners, the final regulations exclude many owners of PTPs from the disclosure rules. 

The identified transactions generally result from either a tax-free distribution of partnership property to a partner that is related to one or more partners of the partnership, or the tax-free transfer of a partnership interest by a related partner to a related transferee.

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The tax-free distribution or transfer generates an increase to the basis of the distributed property or partnership property of $10 million or more ($25 million or more in the case of a TOI undertaken in a tax year before 2025) under the rules of IRC Sections 732(b) or (d), 734(b) or 743(b), but for which no corresponding tax is paid. 

The basis increase to the distributed or partnership property allows the related parties to decrease taxable income through increased cost recovery allowances or decrease taxable gain (or increase taxable loss) on the disposition of the property.

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Treasury, IRS propose rules on commercial clean vehicles, issue guidance on clean fuels

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The Treasury Department and the Internal Revenue Service proposed new rules for the tax credit for qualified commercial clean vehicles, along with guidance on claiming tax credits for clean fuel under the Inflation Reduction Act.

The Notice of Proposed Rulemaking on the credit for qualified commercial clean vehicles (under Section 45W of the Tax Code) says the credit can be claimed by purchasing and placing in service qualified commercial clean vehicles, including certain battery electric vehicles, plug-in hybrid EVs, fuel cell electric vehicles and plug-in hybrid fuel cell electric vehicles.  

The credit is the lesser amount of either 30% of the vehicle’s basis (15% for plug-in hybrid EVs) or the vehicle’s incremental cost in excess of a vehicle comparable in size or use powered solely by gasoline or diesel. A credit up to $7,500 can be claimed for a single qualified commercial clean vehicle for cars and light-duty trucks (with a Gross Vehicle Weight Rating of less than 14,000 pounds), or otherwise $40,000 for vehicles like electric buses and semi-trucks (with a GVWR equal to or greater than 14,000 pounds).

“The release of Treasury’s proposed rules for the commercial clean vehicle credit marks an important step forward in the Biden-Harris Administration’s work to lower transportation costs and strengthen U.S. energy security,” said U.S. Deputy Secretary of the Treasury Wally Adeyemo in a statement Friday. “Today’s guidance will provide the clarity and certainty needed to grow investment in clean vehicle manufacturing.”

The NPRM issued today proposes rules to implement the 45W credit, including proposing various pathways for taxpayers to determine the incremental cost of a qualifying commercial clean vehicle for purposes of calculating the amount of 45W credit. For example, the NPRM proposes that taxpayers can continue to use the incremental cost safe harbors such as those set out in Notice 2023-9 and Notice 2024-5, may rely on a manufacturer’s written cost determination to determine the incremental cost of a qualifying commercial clean vehicle, or may calculate the incremental cost of a qualifying clean vehicle versus an internal combustion engine (ICE) vehicle based on the differing costs of the vehicle powertrains.

The NPRM also proposes rules regarding the types of vehicles that qualify for the credit and aligns certain definitional concepts with those applicable to the 30D and 25E credits. In addition, the NPRM proposes that vehicles are only eligible if they are used 100% for trade or business, excepting de minimis personal use, and that the 45W credit is disallowed for qualified commercial clean vehicles that were previously allowed a clean vehicle credit under 30D or 45W. 

The notice asks for comments over the next 60 days on the proposed regulations such as issues related to off-road mobile machinery, including approaches that might be adopted in applying the definition of mobile machinery to off-road vehicles and whether to create a product identification number system for such machinery in order to comply with statutory requirements. A public hearing is scheduled for April 28, 2025.

Clean Fuels Production Credit

The Treasury the IRS also released guidance Friday on the Clean Fuels Production Credit under Section 45Z of the Tax Code.

Section 45Z provides a tax credit for the production of transportation fuels with lifecycle greenhouse gas emissions below certain levels. The credit is in effect in 2025 and is for sustainable aviation fuel and non-SAF transportation fuels.

The guidance includes both a notice of intent to propose regulations on the Section 45Z credit and a notice providing the annual emissions rate table for Section 45Z, which refers taxpayers to the appropriate methodologies for determining the lifecycle GHG emissions of their fuel. In conjunction with the guidance released Friday, the Department of Energy plans to release the 45ZCF-GREET model for use in determining emissions rates for 45Z in the coming days.

“This guidance will help put America on the cutting-edge of future innovation in aviation and renewable fuel while also lowering transportation costs for consumers,” said Adeyemo in a statement. “Decarbonizing transportation and lowering costs is a win-win for America.”

Section 45Z provides a per-gallon (or gallon-equivalent) tax credit for producers of clean transportation fuels based on the carbon intensity of production. It consolidates and replaces pre-Inflation Reduction Act credits for biodiesel, renewable diesel, and alternative fuels, and an IRA credit for sustainable aviation fuel. Like several other IRA credits, Section 45Z requires the Treasury to establish rules for measuring carbon intensity of production, based on the Clean Air Act’s definition of “lifecycle greenhouse gas emissions.”

The guidance offers more clarity on various issues, including which entities and fuels are eligible for the credit, and how taxpayers determine lifecycle emissions. Specifically, the guidance outlines the Treasury and the IRS’s intent to define key concepts and provide certain rules in a future rulemaking, including clarifying who is eligible for a credit.

The Treasury and the IRS intend to provide that the producer of the eligible clean fuel is eligible to claim the 45Z credit. In keeping with the statute, compressors and blenders of fuel would not be eligible.

Under Section 45Z, a fuel must be “suitable for use” as a transportation fuel. The Treasury and the IRS intend to propose that 45Z-creditable transportation fuel must itself (or when blended into a fuel mixture) have either practical or commercial fitness for use as a fuel in a highway vehicle or aircraft. The guidance clarifies that marine fuels that are otherwise suitable for use in highway vehicles or aircraft, such as marine diesel and methanol, are also 45Z eligible.

Specifically, this would mean that neat SAF that is blended into a fuel mixture that has practical or commercial fitness for use as a fuel would be creditable. Additionally, natural gas alternatives such as renewable natural gas would be suitable for use if produced in a manner such that if it were further compressed it could be used as a transportation fuel.

Today’s guidance publishes the annual emissions rate table that directs taxpayers to the appropriate methodologies for calculating carbon intensities for types and categories of 45Z-eligible fuels.

The table directs taxpayers to use the 45ZCF-GREET model to determine the emissions rate of non-SAF transportation fuel, and either the 45ZCF-GREET model or methodologies from the International Civil Aviation Organization (“CORSIA Default” or “CORSIA Actual”) for SAF.

Taxpayers can use the Provisional Emissions Rate process to obtain an emissions rate for fuel pathway and feedstock combinations not specified in the emissions rate table when guidance is published for the PER process. Guidance for the PER process is expected at a later date.

Outlining climate smart agriculture practices

The guidance released Friday states that the Treasury intends to propose rules for incorporating the emissions benefits from climate-smart agriculture (CSA) practices for cultivating domestic corn, soybeans, and sorghum as feedstocks for SAF and non-SAF transportation fuels. These options would be available to taxpayers after Treasury and the IRS propose regulations for the section 45Z credit, including rules for CSA, and the 45ZCF-GREET model is updated to enable calculation of the lifecycle greenhouse gas emissions rates for CSA crops, taking into account one or more CSA practices.    

CSA practices have multiple benefits, including lower overall GHG emissions associated with biofuels production and increased adoption of farming practices that are associated with other environmental benefits, such as improved water quality and soil health. Agencies across the Federal government have taken important steps to advance the adoption of CSA. In April, Treasury established a first-of-its-kind pilot program to encourage CSA practices within guidance on the section 40B SAF tax credit. Treasury has received and continues to consider substantial feedback from stakeholders on that pilot program. The U.S. Department of Agriculture invested more than $3 billion in 135 Partnerships for Climate-Smart Commodities projects. Combined with the historic investment of $19.5 billion in CSA from the Inflation Reduction Act, the department is estimated to support CSA implementation on over 225 million acres in the next 5 years as well as measurement, monitoring, reporting, and verification to better understand the climate impacts of these practices.

In addition, in June, the U.S. Department of Agriculture published a Request for Information requesting public input on procedures for reporting and verification of CSA practices and measurement of related emissions benefits, and received substantial input from a wide array of stakeholders. The USDA is currently developing voluntary technical guidelines for CSA reporting and verification. The Treasury and the IRS expect to consider those guidelines in proposing rules recognizing the benefits of CSA for purposes of the Section 45Z credit.

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IRS and Treasury propose regs on 401(k) and 403(b) automatic enrollment, Roth IRA catchup contributions

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The Treasury Department and the Internal Revenue Service issued proposed regulations Friday for several provisions of the SECURE 2.0 Act, including ones related to automatic enrollment in 401(k) and 403(b) plans, and the Roth IRA catchup rule.

SECURE 2.0 Act passed at the end of 2022 and contained an extensive list of provisions related to retirement planning, like the original SECURE Act of 2019, with some being phased in over five years.

One set of proposed regulations involves provisions requiring newly-created 401(k) and 403(b) plans to automatically enroll eligible employees starting with the 2025 plan year. In general, unless an employee opts out, a plan needs to automatically enroll the employee at an initial contribution rate of at least 3% of the employee’s pay and automatically increase the initial contribution rate by one percentage point each year until it reaches at least 10% of pay. The requirement generally applies to 401(k) and 403(b) plans established after Dec. 29, 2022, the date the SECURE 2.0 Act became law, with exceptions for new and small businesses, church plans and governmental plans.

The proposed regulations include guidance to plan administrators for properly implementing this requirement and are proposed to apply to plan years that start more than six months after the date that final regulations are issued. Before the final regulations are applicable, plan administrators need to apply a reasonable, good faith interpretation of the statute.

Roth IRA catchup contributions

The Treasury and the IRS also issued proposed regulations Friday addressing several SECURE 2.0 Act provisions involving catch-up contributions, which are additional contributions under a 401(k) or similar workplace retirement plan that generally are allowed with respect to employees who are age 50 or older.

That includes proposed rules related to a provision requiring that catch-up contributions made by certain higher-income participants be designated as after-tax Roth contributions.

The proposed regulations provide guidance for plan administrators to implement and comply with the new Roth catch-up rule and reflect comments received in response to Notice 2023-62, issued in August 2023. 

The proposed regulations also provide guidance relating to the increased catch-up contribution limit under the SECURE 2.0 Act for certain retirement plan participants. Affected participants include employees between the ages of 60-63 and employees in newly established SIMPLE plans.

The IRS and the Treasury are asking for comments on both sets of proposed regulations. 

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