Accounting
Redemptions and reality: Life insurance proceeds and valuation after Connelly
Published
10 months agoon

Succession planning for closely held business owners has always carried estate tax risks, but the Supreme Court’s 2024 decision in
The
If you don’t think the Connelly decision impacts you as a CPA, think again.
First, insurance-funded redemptions with buy-sell agreements are fundamental tools in succession planning. Thousands of closely held businesses have these arrangements in place. As a CPA, you’re likely advising many of these businesses. The Connelly decision essentially pulls the rug out from under established planning strategies.
There’s also professional liability risk. CPAs who continue advising clients using pre-Connelly assumptions could face malpractice claims. Getting qualified appraisals and proper documentation are now more important than ever. More on that in a minute.
Finally, the Connelly decision creates a fundamental disconnect between economic reality and tax valuation. This can lead to double taxation, i.e., both the redemption payment and the underlying proceeds. CPAs involved in business valuations need to understand how this changes their methodology.
Life insurance has long helped closely held businesses provide liquidity for redemptions when an owner dies. These policies are usually paired with buy-sell agreements that mandate redemption, keeping ownership in the intended hands. Until recently, the estate tax consequences of this approach were generally understood and not controversial.
The Connelly ruling puts planning tools at odds with how estate value is measured. It diverges from the Eleventh Circuit’s earlier decision in
What happened in Connelly?
Crown C Supply, a Missouri-based building supply business, was owned by brothers Michael and Thomas Connelly. Their buy-sell agreement gave the surviving brother the first right to purchase the other’s shares, with a mandatory corporate redemption if declined. The company bought $3.5 million of life insurance on each brother. When Michael passed away in 2013, Thomas declined to buy shares, and the company used $3.0 million in life insurance proceeds to redeem Michael’s 77.18% interest.
The purchase price was informally agreed upon, based largely on the insurance proceeds and a $500,000 working capital adjustment, without a formal valuation. It’s important to note that the best practice would be to get a qualified appraisal and attach it to the estate tax return to meet “adequate disclosure” and significantly reduce audit risk.
The estate reported the fair market value of Michael’s shares at $3.0 million. The IRS disagreed, asserting that the full amount of the life insurance should be included in the company’s value. It valued Michael’s interest at $5.3 million (for the addition of the life insurance proceeds, $3.0 million × 77.18% = $2.3 million) triggering about $890,000 in additional estate tax.
The estate paid the tax and sued for a refund. While the District Court sided with the estate, the Eighth Circuit reversed, and the Supreme Court affirmed the IRS’s position. Here’s a
The Supreme Court’s reasoning
Justice Clarence Thomas, writing for a unanimous court, focused on whether a corporate redemption obligation reduces share value under Section 2031 of the Internal Revenue Code. The Supreme Court held that it doesn’t, because the obligation is to shareholders and does not diminish third-party claims. Therefore, the insurance proceeds increased the company’s value, regardless of their use.
This reasoning, however, overlooks the economic substance of the transaction. A rational buyer would never pay $5.3 million for shares knowing the company must immediately pay out $3.0 million. The decision assumes a willing buyer unaware of basic financial facts.
This strategy has been widely used and has long been considered a settled issue from a valuation perspective for the past 20 years.
Revisiting Blount
In Blount, the Eleventh Circuit reached a different conclusion. William Blount owned 83% of a company with a buy-sell agreement and life insurance. The estate reported his shares at $4.0 million, the agreed redemption price. The IRS argued for a higher value, but the court found the proceeds were not available for general use and were offset by the redemption obligation.
The Eleventh Circuit emphasized that life insurance proceeds used solely for redemption do not increase enterprise value. It reasoned that including them artificially inflates estate value without reflecting what a willing buyer would actually pay. This logic shaped estate planning for nearly 20 years—until Connelly reversed course.
Reality meets redemption
In Connelly, the Supreme Court treated the life insurance proceeds as unencumbered assets, despite their required use. Under ASC 480-10-25-4, a mandatory redemption triggered by death would be booked as a liability. The triggering event had occurred, the obligation was measurable, and it likely had priority over other equity in liquidation.
When life insurance is used solely to fund a redemption, the proceeds briefly enter (and exit) the balance sheet. They do not enhance income potential or provide capital that can be used for distribution. What exists is a transitory moment of increased cash immediately followed by a mandatory outflow, structure or long-term value. Treating them as accretive misstates the buyer’s actual position.
This results in a double taxation that would make a C corp blush. The estate receives the redemption payment yet is taxed again as if those proceeds increased the business’s value. In large estates, this can leave little to nothing after tax. Fair market value should reflect a real-world transaction between a willing buyer and willing seller; it should not reflect accounting entries in isolation.
In Blount, the Eleventh Circuit got this right with substance over form. Insurance proceeds used for redemption do not enhance enterprise value. They merely support ownership transition. Including them in value ends up mistaking cash movement for the creation of wealth.
The Connelly decision complicates estate planning, but it does not replace the need for careful valuation analysis. It is now more important than ever to distinguish between temporary funding mechanisms and true value accretion. A qualified appraisal remains the best defense in an estate tax audit, reducing the risk of added tax and penalties. Advisors should reassess plans that rely on insurance-funded redemptions.
CPAs who understand these implications can provide superior advisory services, helping clients navigate the new landscape while competitors may still be operating under outdated assumptions.
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The Financial Accounting Standards Board met this week to discuss its projects on accounting for transfers of cryptocurrency assets and enhancing the disclosures around certain digital assets, such as stablecoins.
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During Wednesday’s meeting, FASB’s board made certain tentative decisions, according to a
At a future meeting, the board plans to consider clarifying the derecognition guidance for crypto transfer arrangements to assess whether the control of a crypto asset has been transferred.
FASB also began deliberations on the
The board decided to provide illustrative examples in Topic 230, Statement of Cash Flows, to clarify whether certain digital assets such as stablecoins can meet the definition of cash equivalents. It also decided to include the following concepts in the illustrative examples:
- Interpretive explanations that link to the current cash equivalents definition;
- The amount and composition of reserve assets; and,
- The nature of qualifying on-demand, contractual cash redemption rights directly with the issuer.
FASB plans to clarify that an entity should consider compliance with relevant laws and regulations when it’s creating a policy concerning which assets that satisfy the Master Glossary definition of the term “cash equivalents“ will be treated as cash equivalents.
“I agree with the staff suggestion to look at examples,” said FASB vice chair Hillary Salo. “From my perspective, I think that is going to help level the playing field. People have been making reasonable judgments. I agree with that. And I think that this is really going to help show those goalposts or guardrails of what types of stablecoins would be in the scope of cash equivalents, and which ones would not be in the scope of cash equivalents. I certainly appreciate that approach, and I think it has the least potential impact of unintended consequences, because I do agree with my fellow board members that we shouldn’t be changing the definition of cash equivalents, and it’s a high bar to get into the cash equivalent definition.”
“I’m definitely supportive of not changing the definition of cash equivalents,” said FASB chair Richard Jones. “I believe that’s settled GAAP in a way, and we’re not really seeing a call to change it for broader issues. I am supportive of the example-based approach. The challenge with examples, though, is everybody’s going to want their exact pattern, but that’s not what we’re doing.”
The examples will explain the rationale for how digital assets such as stablecoins do or do not qualify as cash equivalents and give a roadmap for other types of digital assets with varying fact patterns to be able to apply.
“We really don’t want to be as a board facing a situation where something was a cash equivalent and then no longer is at a later date,” said Jones. “That’s not good for anyone, so keeping it as a high bar with certain rigid criteria, I think, is fine.”
Stablecoins are supposed to be pegged to fiat currencies such as U.S. dollars and thus provide more stability to investors. “In my view, while a stablecoin may meet the accounting definition established for cash equivalents, not every one of those stablecoins in the cash equivalent classification represents the same level of risk,” said FASB member Joyce Joseph.
She noted that the capital markets recognize the distinctions and have established a Stablecoin Stability Assessment Framework to evaluate a stablecoin’s ability to maintain its peg to a fiat currency. Such assessments look at the legal and regulatory framework associated with the stablecoin, and provide investors with information that could enable them to do forward-looking assessments about the stability of the stablecoin.
“However, for an investor to consider and utilize such information for a company analysis the financial statement disclosures would need to include information about the stablecoin itself,” Joseph added. “In outreach, the staff learned that investors supported classifying certain stablecoins as cash equivalents when transparent information is available about the entities at which the reserve assets are held. Therefore, in my view, taking all of this into consideration a relevant and informative company disclosure would include providing investors with the name of the stablecoin and the amount of the stablecoin that is classified as a cash equivalent, so investors can independently assess the liquidity risks more meaningfully and more comprehensively by utilizing broader information that is available in the capital markets and its emerging information.”
Such information could include the issuer, reserves, governance and management, she noted, so investors would get a more holistic look at the risks that holding the stablecoin would entail for a given company.
The board decided to require all entities to disclose the significant classes and related amounts of cash equivalents on an annual basis for each period that a statement of financial position is presented.
Entities should apply the amendments related to the classification of certain digital assets as cash equivalents on a modified prospective basis as of the beginning of the annual reporting period in the year of adoption.
FASB decided that entities should apply the amendments related to the disclosure of the significant classes and amounts of cash equivalents on a prospective basis as of the date of the most recent statement of financial position presented in the period of adoption.
The board will allow early adoption in both interim and annual reporting periods in which financial statements have not been issued or made available for issuance.
FASB also decided to permit entities to adopt the amendments to be illustrated in the examples related to the classification of certain digital assets as cash equivalents without the need to perform a preferability assessment as described in Topic 250, Accounting Changes and Error Corrections.
The board directed the staff to draft a proposed accounting standards update to be voted on by written ballot. The proposed update will have a 90-day comment period.
Accounting
Lawmakers propose tax and IRS bills as filing season ends
Published
2 weeks agoon
April 17, 2026

Senators introduced several pieces of tax-related legislation this week, including measures aimed at improving customer service at the Internal Revenue Service, cracking down on tax evasion and curbing the carried interest tax break, in addition to efforts in the House to repeal the Corporate Transparency Act.
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Senators Bill Cassidy, R-Louisiana, and Mark Warner, D-Virginia, teamed up on introducing a bipartisan bill, the
The bill would establish a dashboard to inform taxpayers of backlogs and wait times; expand electronic access to information and refunds; expand callback technology and online accounts; and inform individuals facing economic hardship about collection alternatives.
“Taxpayers deserve a simple, stress-free experience when dealing with the IRS,” Cassidy said in a statement Wednesday. “This bill makes the process quicker and easier for taxpayers to get the information they need.”
He also mentioned the bill during a
“I’m happy to meet with the team … and do all I can to make it as good as you want it to be,” said Bisignano.
“My bill would equip the IRS with the legislative mandate to create an online dashboard so that taxpayers can monitor average call wait time and budget time accordingly,” said Cassidy. He noted that the bill would allow a callback for taxpayers that might need to wait longer than five minutes to speak to a representative, and establish a program to identify and support taxpayers struggling to make ends meet by providing information about alternative payment methods, such as installments, partial payments and offers in compromise.
“I know people are kind of desperate and don’t know where to turn for cash, so I think this could really ease anxiety,” he added. “This legislation is bipartisan and is likely to pass this Congress.”
Cassidy and Warner
“Taxpayers shouldn’t have to jump through hoops to get basic answers from the IRS — and in the last year, those challenges have only gotten worse,” Warner said in a statement. “I am glad to reintroduce this bipartisan legislation on Tax Day to ease some of this frustration by increasing clear communication and making IRS resources more readily available.”
Stop CHEATERS Act
Also on Tax Day, a group of Senate Democrats and an independent who usually caucuses with Democrats teamed up to introduce the Stop Corporations and High Earners from Avoiding Taxes and Enforce the Rules Strictly (Stop CHEATERS) Act.
Senate Finance Committee ranking member Ron Wyden, D-Oregon, joined with Senators Angus King, I-Maine, Elizabeth Warren, D-Massachusetts, Tim Kaine, D-Virginia, and Sheldon Whitehouse, D-Rhode Island. The bill would provide additional funding for the IRS to strengthen and expand tax collection services and systems and crack down on tax cheating by the wealthy.
“Wealthy tax cheats and scofflaw corporations are stealing billions and billions from the American people by refusing to pay what they legally owe, and far too many of them are getting a free pass because Republicans gutted the enforcement capacity of the IRS,” Wyden said in a statement. “A rich tax cheat who shelters mountains of cash among a web of shell companies and passthroughs is likelier to be struck by lightning than face an IRS audit, and Republicans want to keep it that way. This bill is about making sure the IRS has the resources it needs to go after wealthy tax cheats while improving customer service for the vast majority of American taxpayers who follow the law every year.”
Earlier this week. Wyden also
The Stop CHEATERS Act would provide the IRS with additional funding for tax enforcement focused upon high-income tax evasion, technology operations support, systems modernization, and taxpayer services like free tax-payer assistance.
“As Congress seeks ways to fund much-needed policy priorities and address our growing national debt, there is one common sense solution that should have unanimous bipartisan support: let’s enforce the tax laws already on the books,” said King in a statement. “Our legislation will make sure the IRS has the resources it needs to confront the gap between taxes owed and taxes paid – while ensuring that our tax enforcement professionals are focused on the high-income earners who account for the most tax evasion. This is a serious problem with an easy solution; let’s pass this legislation and make sure every American pays what they owe in taxes.”
Carried interest
Wyden, King and Whitehouse also teamed up on another bill Thursday to close the carried interest tax break for hedge fund managers that
Carried interest is a form of compensation received by a fund manager in exchange for investment management services, according to a
Under the bill, the
“Our tax code is rigged to favor ultra-wealthy investors who know how to game the system to dodge paying a fair share, and there is no better example of how it works in practice than the carried interest loophole,” Wyden said in a statement. “For several decades now we’ve had a tax system that rewards the accumulation of wealth by the rich while punishing middle-class wage earners, and the effect of that system has been the strangulation of prosperity and opportunity for everybody but the ultra-wealthy. There are a lot of problems to fix to restore fairness and common sense to our tax code, and closing the carried interest loophole is a great place to start.”
Repealing Corporate Transparency Act
The House Financial Services Committee is also planning to markup a bill next Tuesday that would fully repeal the Corporate Transparency Act, which has already been significantly
If enacted, the repeal would eliminate beneficial ownership reporting requirements, removing a transparency measure designed to help law enforcement and national security officials identify who is behind U.S. companies.
“This repeal would turn the United States back into one of the easiest places in the world to set up anonymous shell companies, something Congress worked for years to fix,” said Erica Hanichak, deputy director of the FACT Coalition, in a statement. “These entities are routinely used to facilitate corruption, financial crime, and abuse. Rolling back the CTA doesn’t just weaken transparency, it signals to bad actors around the world that the U.S. is once again open for illicit business.”
Accounting
IRS struggles against nonfilers with large foreign bank accounts
Published
3 weeks agoon
April 15, 2026

The Internal Revenue Service rarely penalizes taxpayers who have high balances in foreign bank accounts and fail to file the proper forms, according to a new report.
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The
Taxpayers with specified foreign financial assets that meet a certain dollar threshold are also required to report the information to the IRS by filing Form 8938. Failure to file the form can result in penalties of up to $60,000. However, TIGTA’s previous reports have demonstrated that the IRS rarely enforces these penalties.
The IRS created an Offshore Private Banking Campaign initiative to address tax noncompliance related to taxpayers’ failure to file Form 8938 and information reporting associated with offshore banking accounts, but it’s had limited success.
Even though the initiative identified hundreds of individual taxpayers with significant foreign bank account deposits who failed to file Forms 8938, the campaign only resulted in relatively few taxpayer examinations and a small number of nonfiling penalties. The campaign identified 405 taxpayers with significant foreign account balances who appeared to be noncompliant with their FATCA reporting requirements.
The IRS used two ways to address the 405 noncompliant taxpayers: referral for examinations and the issuance of letters to them.
- 164 taxpayers (who had an average unreported foreign account balance of $1.3 billion) were referred for possible examination, but only 12 of the 164 were examined, with five having $39.7 million in additional tax and $80,000 in penalties assessed.
- 241 noncompliant taxpayers (who had an average unreported account balance of $377 million) received a combination of 225 educational letters (requiring no response from the taxpayers) and 16 soft letters (requiring taxpayers to respond). None of the 241 taxpayers were assessed the initial $10,000 FATCA nonfiling penalty.
“While taxpayers can hold offshore banking accounts for a number of legitimate reasons, some taxpayers have also used them to hide income and evade taxes,” said the report.
Significant assets and income are factors considered by the IRS when assessing whether taxpayers intentionally evaded their tax responsibilities, the report noted. Given the large size of the average unreported foreign account balances, these taxpayers probably have higher levels of sophistication and an awareness of their obligation to comply with the law.
TIGTA believes the IRS needs to establish specific performance measures to determine the effectiveness of the FATCA program. “If the IRS does not plan to enforce the FATCA provisions even where obvious noncompliance is identified, it should at least quantify the enforcement impact of its efforts,” said the report. “This will ensure that IRS decision makers have the information they need to determine if the FATCA program is worth the investment and improves taxpayer compliance.
TIGTA made three recommendations in the report, including revising Campaign 896 processes to include assessing FATCA failure to file penalties; assessing the viability of using Form 1099 data to identify Form 8938 nonfilers; and implementing additional performance measures to give decision makers comprehensive information about the effectiveness of the FATCA program. The IRS disagreed with two of TIGTA’s recommendations and partially agreed with the remaining recommendation. IRS officials didn’t agree to assess penalties in Campaign 896 or with implementing performance measures to assess the effectiveness of the FATCA program.
“From our perspective, TIGTA’s conclusions regarding IRS Campaign 896 are based, in part, on a misguided premise and overgeneralizations, including the treatment of ‘potential noncompliance’ as tantamount to ‘egregious noncompliance’ that warrants a monetary penalty without contemplating the variety of justifications that may exempt a taxpayer from having to file Form 8938,” wrote Mabeline Baldwin, acting commissioner of the IRS’s Large Business and International Division, in response to the report.
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