LLCs Run Through It

What do you think of when someone mentions Montana? Is it the seemingly boundless landscape from which the largest land-locked state[i] derived its nickname, Big Sky Country?[ii] What about its Rocky Mountain national parks, like Glacier or Yellowstone?[iii]

Until recently, I had always equated Montana with rugged landscapes, honest outdoor living,[iv] flyfishing,[v] and my grandfather.[vi]

Of late, however, Montana, or more accurately, the use of Montana LLCs, has become synonymous with sales tax avoidance (or worse).

Continue Reading Sales Tax Savings With Montana LLCs? Don’t Do It

Tax Deficiency

Over their career, every tax practitioner has had many client-taxpayers against whom a government’s taxing authority – be it federal, state, or local – has asserted and then assessed a tax deficiency.

There are many reasons why a taxpayer – whether an individual, corporation, partnership, estate or trust – has unpaid tax liabilities. For example, the taxpayer has: miscalculated the amount of tax owed, carelessly omitted an item of income, mistakenly deducted a non-deductible expense, or claimed a tax treatment for an item on their tax return with which the government disagreed.

Continue Reading Applying the Federal Priority Statute to The Attorney as Client’s “Corporate Executive”

Non-Recognition Exchanges

Under the Code and the Regulations issued thereunder, the gain or loss arising from the conversion of property into cash is treated as income realized or as loss sustained by the owner of the converted property,[i] which the owner must generally account for in determining their federal income tax liability for the year of the conversion.[ii]

Likewise, the gain or loss arising from a property owner’s exchange of such property for other property that differs “materially in kind” from the property exchanged should, as in the case of a sale for cash, be treated as a taxable event, the gain or loss from which must be accounted for in determining the owner’s gross income for the year of the exchange.[iii] 

Continue Reading Tax-free Conversion of Corporation Into Partnership Via “C” Reorganization

Near Death Experience

Stick a fork in it. It’s kaput.[i] At least that’s what many of us thought; and, for all intents and purposes, it was.

However, like a scene from a bad zombie movie,[ii] the corpse-like Corporate Transparency Act (the “CTA”) may have just been resuscitated, at least temporarily.[iii]

This legal reanimation of the CTA coincides, “fortuitously” you might say, with the effective date of New York’s own version of the federal law, the LLC Transparency Act (the “LLCTA”),[iv] which became effective on January 1,2026.

LLCTA

For the most part, New York’s LLCTA is based upon the federal CTA; for example, it defines the key terms “beneficial owner”[v] and “reporting company” by reference to the CTA and its implementing regulations,[vi] though the New York statute does not reach beyond limited liability companies (“LLCs”).

Although the effective date of the New York disclosure rule had been known since it was amended in March 2024,[vii] the law’s actual coverage became somewhat uncertain following the issuance by the Financial Crimes Enforcement Network (“FinCEN”) of an “interim final rule” – i.e., implementing regulations – on March 26, 2025 (see below), which limited the definition of “reporting company” for purposes of the CTA to mean only entities that are formed under the law of a foreign country.

NY Amendment?

In response to FinCEN’s interim final rule, and to ensure the LLCTA would continue to cover the beneficial owners of domestic business entities, the New York Legislature, in June 2025, passed amendments to the LLCTA that would have directly incorporated the CTA’s statutory definitions – including, for example, that for a reporting company – but without reference to any implementing federal regulations, in order to “inoculate the LLC Transparency Act from shifting federal guidelines or attempts to repeal the CTA.”[viii]

After a period of uncertainty and speculation, Governor Hochul vetoed the proposed amendment on December 19, 2025 – less than two weeks before the effective date of the LLCTA – thereby continuing New York’s “conformity” to the federal regulatory interpretation of the CTA, which limits that law’s coverage to foreign (non-U.S.) LLCs authorized to do business in the State.[ix]

Thus, we began 2026 with some certainty regarding the scope of the federal CTA and of New York’s LLCTA.

Or did we?

Unresolved Challenges?

To better understand where we are today, it would help to review some relevant history.

As we’ll see shortly, it didn’t take long after the enactment of the CTA for businesses to challenge its constitutionality in the federal courts on the grounds that the CTA exceeded: (i) Congress’s enumerated powers to regulate interstate commerce[x] and to “lay and collect taxes,”[xi] and its interest in advancing the national security and foreign policy interests of the U.S.; and (ii) its authority to enact such laws as are “necessary and proper”[xii] to carry out the foregoing powers.

How Did We Get Here?

In December 2020, Congress sent the CTA to the President for his signature. Although the Administration supported the CTA,[xiii] it was included in the bill for the National Defense Authorization Act, which the President vetoed for reasons unrelated to the CTA. As we know, his veto was overridden[xiv] and the bill thereby became law, effective January 1, 2021.[xv]

You’ll recall that the CTA required “reporting companies” to submit specified beneficial ownership information (“BOI”) to FinCEN.[xvi]

However, the statutory requirement for reporting companies to submit BOI was to take effect “on the effective date of the regulations” implementing the reporting obligations.[xvii]

Under the CTA, reporting companies created or registered to do business after the effective date were required to submit the requisite information to FinCEN at the time of creation or registration, while reporting companies in existence before the effective date would have a specified period within which to report.[xviii]

FinCEN issued final BOI reporting rules on September 30, 2022, with an effective date of January 1, 2024.[xix]

Soon after the “final” reporting rules were issued, the first of several legal challenges to the CTA was initiated when, in November 2022, National Small Business United filed a complaint in the U.S. District Court for the Northern District of Alabama claiming the CTA exceeded Congress’s enumerated powers[xx] and, therefore, was unconstitutional (the “NSBU litigation”).

On March 1, 2024 – only two months after the reporting rules became effective – the U.S. District Court in the NSBU litigation concluded that the CTA was “unconstitutional because it cannot be justified as an exercise of Congress’s enumerated powers” – it did not regulate commercial or economic activity but only the act of incorporation. With that, the District Court enjoined FinCEN from enforcing the Act against the plaintiffs.[xxi]

On March 11, the Justice Department filed a Notice of Appeal to the Eleventh Circuit Court of Appeals on behalf of the Treasury;[xxii] the Circuit Court granted expedited review and scheduled oral Arguments for September 27, 2024.

That same day, FinCEN issued a notice in which it stated that, while the NSBU litigation was ongoing, FinCEN would continue to implement the Act as required by Congress, while complying with the District Court’s order; thus, other than the individuals and entities subject to the District Court’s injunction, all other reporting companies were still required to comply with the CTA and file BOI reports as provided in FinCEN’s regulations.[xxiii]

On April 29, 2024, a bill was introduced in the House to repeal the CTA;[xxiv] the bill was referred to the House Committee on Financial Services. A similar bill was introduced into the Senate on May 9; it was referred to the Senate Committee on Banking, Housing, and Urban Affairs.[xxv] Not surprisingly, no further action has been taken on either bill.

On May 20, 2024, twenty-two States joined in filing an amicus brief with the Eleventh Circuit in which they urged the Court to affirm the March 1 decision by the District Court in Alabama, based largely on principles of federalism.[xxvi]

On July 18, the Eleventh Circuit scheduled oral argument in the NSBU litigation for September 27, 2024, and on August 14 the Court requested that the parties submit supplemental briefs regarding whether the District Court erred “in not holding the plaintiffs to their burden of showing that there are no constitutional applications of the Corporate Transparency Act.”[xxvii]

On September 27, a three-judge panel of the Eleventh Circuit heard oral arguments in the NSBU litigation.[xxviii]

On November 5, 2024, the Republicans won the White House, and the 119^th Congress[xxix] was set to begin with a narrow Republican majority in both Chambers.

On December 17, House Speaker Johnson unveiled a continuing resolution that would have extended by one year the deadline for existing companies to report their BOI to FinCEN, as required under the CTA.[xxx]

On December 27, in response to an order issued by a panel of the Fifth Circuit, FinCEN issued an alert stating: “In light of a recent federal court order, reporting companies are not currently required to file beneficial ownership information with FinCEN and are not subject to liability if they fail to do so while the order remains in force. However, reporting companies may continue to voluntarily submit beneficial ownership information reports.”[xxxi]

A Different Approach

On March 2, 2025, the Treasury Department announced, with respect to the CTA, that it would not enforce any penalties or fines associated with the BOI reporting rule under the existing regulatory deadlines, and that it would not enforce any penalties or fines against U.S. citizens or U.S. reporting companies or their beneficial owners after the issuance of proposed rulemaking that would narrow the scope of the disclosure rule to foreign reporting companies only.[xxxii] 

Consistent with the foregoing announcement, on March 21 FinCEN announced that it was issuing an interim final rule that would remove the requirement for U.S. companies and U.S. persons to report BOI to FinCEN under the CTA.[xxxiii]

The Interim Final Rule

The interim final rule was issued on March 26 and eliminated the requirement for U.S. companies and U.S. persons to report BOI to FinCEN under the CTA.[xxxiv]

Specifically, FinCEN revised the definition of “reporting company” in its implementing regulations to mean only those entities that are formed under the law of a foreign country and that have registered to do business in the any U.S. State by the filing of a document with a secretary of state or similar office. FinCEN also exempted entities previously known as “domestic reporting companies” from BOI reporting requirements.

Thus, through this interim final rule, all entities created in the U.S. and their beneficial owners were exempted from the requirement to report BOI to FinCEN.

However, entities that met the new definition of a “reporting company” and did not qualify for an exemption from the reporting requirements were required to report their BOI to FinCEN under new deadlines.

These foreign entities, however, were not be required to report any U.S. persons as beneficial owners, and U.S. persons were not required to report BOI with respect to any such entity in which they were a beneficial owner.[xxxv]

Why the Change?

The interim final rule is ostensibly rooted in the Treasury Department’s authority under the CTA to exempt any “entity or class of entities” for which the Secretary of the Treasury, with the written concurrence of the Attorney General and the Secretary of Homeland Security, has determined that “requiring beneficial ownership information from the entity or class of entities” – in this case, the class comprising domestic reporting companies and their beneficial owners – “would not serve the public interest” and “would not be highly useful in national security, intelligence, and law enforcement agency efforts to detect, prevent, or prosecute money laundering, the financing of terrorism, proliferation finance, serious tax fraud, or other crimes.”[xxxvi]

By contrast, the Treasury Department determined that foreign reporting companies – other than those the beneficial owners of which are all U.S. persons – present heightened national security and illicit finance risks.

At the same time, however, the Administration continued to support the constitutionality of the CTA in actions regarding the law’s application to domestic companies.[xxxvii]

How do we reconcile this support with the Treasury Department’s narrow implementation of the CTA?

Did it reflect the Administration’s unstated determination that the broadly drafted CTA may be difficult to defend under the Constitution’s interstate commerce and taxing clauses, whereas a narrower implementation that was limited to foreign entities, and that focused on issues relating to national security and foreign commerce, had a higher probability of withstanding any challenge?   

Or was there a change in stance toward the CTA? As Treasury Secretary Bessent was quoted in the March 2 FinCEN announcement, “Today’s action is part of President Trump’s bold agenda to unleash American prosperity by reining in burdensome regulations, in particular for small businesses that are the backbone of the American economy.”

Then, toward the end of 2025, the Eleventh Circuit Court of Appeals issued its opinion in the NSBU litigation.[xxxviii]

The Eleventh Circuit

The issue before the Court was whether the CTA is constitutional.

According to the Court, most states do not require businesses to report information about their owners. The Court explained that bad actors were using the anonymity afforded by state corporate laws to commit financial crimes, such as money laundering and financing terrorism; i.e., crimes “affecting interstate and international commerce.” Congress, the Court continued, found that this information gap hampered law enforcement’s efforts to fight such crimes.  

To prevent these anonymous business dealings, the Court stated, Congress passed the CTA, which requires certain corporate entities to report their “beneficial owners” – i.e., the actual people who exercise control over the entity – to the Treasury Department.

The Court stated that, in order to be constitutional, every federal law must be consistent with one of Congress’s enumerated powers and must not violate any of the Constitution’s guarantees of individual rights.

The plaintiff, National Small Business United – a business association representing “over 65,000 businesses . . . located in all 50 states,” with members from every sector of the U.S. economy – argued that the CTA failed on both counts. It claimed that the CTA was not an appropriate exercise of Congress’s power to regulate interstate commerce[xxxix] and was therefore facially unconstitutional. In the alternative, the plaintiff asserted that the CTA violated the Fourth Amendment’s prohibition on unreasonable searches and was facially unconstitutional for that reason.

The District Court had concluded that the CTA did not regulate economic activity and, on that basis, granted summary judgment for the plaintiff.  

According to the District Court, neither the commerce, taxing, and necessary and proper clauses, nor Congress’s foreign affairs and national security powers, justified the CTA. Regarding the Commerce Clause, the court ruled that the CTA primarily regulates the non-commercial act of incorporation and that the connection between the act of incorporation and the activities Congress sought to curb was too attenuated. The court also emphasized the lack of any “jurisdictional hook” in the CTA that limited its reach to interstate commerce.

The Court of Appeals disagreed with the lower court’s decision, and found that, by effectively prohibiting anonymous business dealings, the CTA facially regulated economic activities having a “substantial aggregate impact” on interstate commerce.

According to the Court, the CTA is a constitutional exercise of Congress’s power under the Commerce Clause. By regulating activity that is economic in nature,[xl] it effectively “prohibits anonymous corporate dealings, regulates commercial entities that are active in the stream of commerce,” and requires them to report information related to their ownership.

The Court also determined that Congress had rationally concluded, based on input from numerous national security and law enforcement experts about how anonymous shell companies affect interstate and international commerce, that anonymous corporate dealings have a substantial aggregate effect on interstate commerce.

Moreover, as a uniform and limited reporting requirement, the CTA did not facially violate the Fourth Amendment.[xli]

Accordingly, the Court of Appeals reversed the District Court.

Where Does That Leave Us?

The Circuit Court’s opinion supports the scope of the CTA as enacted, as well as FinCEN’s original interpretation of the legislation – both of which are being supported by the Administration in ongoing litigation.

In contrast, there is FinCEN’s interim final rule and the stated justification for its limited implementation of the CTA.

Query how the Court’s decision may affect the outcomes of the ongoing challenges to the CTA on constitutional grounds in other circuits.

Query also whether the Court’s decision may embolden the Administration to use its regulatory authority under the CTA to expand its implementation to cover domestic reporting entities.

Time will tell.

The opinions expressed herein are solely those of the author(s) and do not necessarily represent the views of the firm.

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[i] Of course, the title reference to “mostly dead” comes from Miracle Max in The Princess Bride: “There’s a big difference between mostly dead and all dead. Mostly dead is slightly alive.”

[ii] Are there any good ones?

[iii] As we’ll see shortly, it appears the Eleventh Circuit was not provided a copy of the CTA’s Do Not Resuscitate order. These things happen.

[iv] LLCL Sec. 1106. Enacted December 22, 2023. S. 995B/A.3484-A.

[v] LLCL Sec. 1106(a):

“‘Beneficial owner’ shall have the same meaning as defined in 31 U.S.C. § 5336(a)(3), as amended, and any regulations promulgated thereunder.”

[vi] LLCL Sec. 1106(b):

“‘Reporting company’ shall have the same meaning as defined in 31 U.S.C. § 5336(a)(11), as amended, and any regulations promulgated thereunder, but shall only include limited liability companies formed or
authorized to do business in New York state.”

[vii] The LLCTA was originally set to go into effect in late 2024.

[viii] See the Sponsor Memo to S8432.

[ix] Shortly thereafter, New York’s Department of State posted guidance on its website to assist foreign LLCs with reporting their beneficial ownership in accordance with the LLCTA. https://dos.ny.gov/beneficial-owner-disclosure.

[x] The Constitution of the United States, Article I, Section 8, Clause 3.

[xi] The Constitution of the United States, Article I, Section 8, Clause 1.

[xii] The Constitution of the United States, Article I, Section 8, Clause 18.  

[xiii] https://thefactcoalition.org/fact-sheet-a-brief-summary-of-the-corporate-transparency-act-of-2019-title-lxiv-of-the-ndaa-h-r-6395/.

[xiv] The House voted 322-87, and the Senate voted 81-13, to override the veto.

[xv] The Constitution of the United States, Article I, Section 7, Clause 2.

[xvi] 31 U.S.C. 5336.

[xvii] 31 U.S.C. 5336(b)(5): ‘‘(5) EFFECTIVE DATE — The requirements of this subsection shall take effect on the effective date of the regulations prescribed by the Secretary of the Treasury under this subsection, which shall be promulgated not later than 1 year after the date of enactment of this section.”

[xviii] 31 U.S.C. 5336(b)(1)(B), (C).

[xix] Published Document: 2022-21020 (87 FR 59498). As issued, the rules required (a) companies formed before January 1, 2024 to file a BOI report with FinCEN by December 31, 2024, and (b) companies created on or after the rule’s effective date (of January 1, 2024) and before January 1, 2025, to file within 30 calendar days of notice of their creation.

About one year later, the reporting rules were amended to provide an extended filing deadline of 90 calendar days for reporting companies created on or after January 1, 2024 and before January 1, 2025; entities created on or after January 1, 2025 would continue to have 30 calendar days from notice of their creation to file their BOI reports with FinCEN. Published Document: 2023-26399 (88 FR 83499).

[xx] The Constitution of the United States, Article I, Section 8.

[xxi] National Small Business United, d/b/a National Small Business Association, et al., v. Janet Yellen, in her official capacity as Secretary of the Treasury, et al., No. 5:22-cv-01448 (N.D. Ala.).

[xxii] National Small Business United et al. v. U.S. Department of the Treasury et al., case number 24-10736, in the U.S. Court of Appeals for the Eleventh Circuit.

[xxiii] https://www.fincen.gov/news/news-releases/updated-notice-regarding-national-small-business-united-v-yellen-no-522-cv-01448

[xxiv] H.R.8147, the “Repealing Big Brother Overreach Act”. 

[xxv] S.4297.

[xxvi] https://assets.law360news.com/1839000/1839407/https-ecf-ca11-uscourts-gov-n-beam-servlet-transportroom-servlet-showdoc-011013344879.pdf,: Alabama, Arkansas, Florida, Georgia, Idaho, Iowa, Kansas, Kentucky, Louisiana, Mississippi, Missouri, Montana, Nebraska, Ohio, South Carolina, South Dakota, Tennessee, Texas, Utah, Virginia, West Virginia, and Wyoming.

[xxvii] https://www.courtlistener.com/docket/68332749/national-small-business-united-v-us-department-of-the-treasury/ 

[xxviii] Supplemental authorities were filed in the Eleventh Circuit’s NSBU case on December 4 and 5.

[xxix] The 2025–2027 term.

[xxx] You may recall that the then President-elect opposed this Continuing Resolution, Sec. 122 of which read as follows:

Section 5336(b)(1)(B) of title 31, United States Code, is amended by striking ‘‘before the effective date of the regulations prescribed under this subsection shall, in a timely manner, and not later than 2 years after the effective date of the regulations prescribed under this subsection,’’ and inserting ‘‘before January 1, 2024, shall, not later than January 1, 2026,’’

[xxxi] FinCEN referenced an order issued by a panel of the Fifth Circuit vacating an earlier panel’s December 23 order that had granted a stay of the preliminary injunction in the Texas Top Cop Shop case, thereby restoring the injunction issued by the District Court in that case and relieving reporting companies from the requirement to file BOI with FinCEN.

[xxxii] https://home.treasury.gov/news/press-releases/sb0038#:~:text=The%20Treasury%20Department%20is%20announcing,January%202%2C%202026

[xxxiii] https://www.fincen.gov/news/news-releases/fincen-removes-beneficial-ownership-reporting-requirements-us-companies-and-us

[xxxiv] https://www.federalregister.gov/documents/2025/03/26/2025-05199/beneficial-ownership-information-reporting-requirement-revision-and-deadline-extension

According to the Preamble to the interim final rule:

“On January 20, 2025, there was a change in presidential administrations, which has resulted in a reassessment of the balance struck by the Reporting Rule. On January 31, 2025, President Trump issued Executive Order (E.O.) 14192, Unleashing Prosperity Through Deregulation, which announced an Administration policy “to significantly reduce the private expenditures required to comply with Federal regulations to secure America’s economic prosperity and national security and the highest possible quality of life for each citizen” and “to alleviate unnecessary regulatory burdens placed on the American people.” Consistent with the exemptive authority provided in the CTA and the direction of the President, the Secretary has reassessed the balance between the usefulness of collecting BOI and the regulatory burdens imposed by the scope of the Reporting Rule.”

[xxxv] FinCEN also issued some helpful questions and answers (Q&As) in anticipation of inquiries relating to the interim final rule. https://www.fincen.gov/boi/ifr-qa

[xxxvi] 31 U.S.C. 5336(a)(11)(B)(xxiv).

[xxxvii] For example, it filed a brief with the Fifth Circuit in February of 2025, in the Texas Top Cop Shop case, in which it sought a stay of the nationwide injunction against the federal government’s enforcement of the CTA issued by the district court. https://www.taxnotes.com/research/federal/court-documents/court-petitions-and-briefs/government-urges-court-reverse-transparency-act-injunction/7r16q. 

[xxxviii] https://media.ca11.uscourts.gov/opinions/pub/files/202410736.pdf

[xxxix] The Constitution of the United States, Article I, Section 8, Clause 3.

[xl] A law can regulate economic activity, the Court stated, even if the connection between the challenged law and commerce isn’t “airtight.” It is enough that the regulated activity involves “some sort of economic endeavor” with “an apparent commercial character.”

[xli] The Fourth Amendment protects “[t]he right of the people to be secure in their persons, houses, papers, and effects, against unreasonable searches and seizures.”

Tax Savings and Deal Economics

It is a basic tax principle that the more (or the sooner) a seller pays in taxes on the sale of its business, the less will be the economic benefit the seller realizes from the sale. Similarly, the fewer the tax savings that the buyer realizes from the acquisition of the business, the less will be the economic benefit the buyer realizes from the acquisition.[i]

Allocation of Purchase Price

In most cases, these “truths” are first considered in determining the form of the transaction – a purchase and sale of assets or of stock. They become prominent again in the context of allocating the consideration[ii] actually, or deemed to have been,[iii] paid and received for the actual or deemed purchase and sale of the assets comprising the business.

Continue Reading When a Buyer’s “Tax Cost” for an Acquisition Exceeds Expectations