News & Analysis as of

Internal Revenue Service Insurance Industry Tax Court

The United States Internal Revenue Service is a bureau of the United States Department of the Treasury. The IRS is charged with collecting revenue and enforcing the Internal Revenue Code.  
Downs Rachlin Martin PLLC

Captive Insurance Update | Issue 2 | 2025

Every year, the members of the Vermont Captive Insurance Association’s legislative committee and the Vermont Department of Financial Regulation (the “DFR”) work to improve Vermont’s captive insurance laws and regulations....more

ArentFox Schiff

Health Care Provider Loses Tax-Exempt Status in Fifth Circuit Decision

ArentFox Schiff on

On October 28, the US Court of Appeals for the Fifth Circuit held that a nonprofit corporation that coordinates health care for privately insured patients does not qualify for tax exemption under Section 501(c)(4) because it...more

Downs Rachlin Martin PLLC

What Connelly v. United States Means for Closely-Held Businesses

The US Supreme Court recently issued a significant decision, impacting many closely-held businesses with buy-sell agreements funded by life insurance policies, Connelly v. United States, 144 S. Ct. 1406 (2024). In a 9-0...more

Carlton Fields

Tax Court Upholds IRS Decision That Premiums Paid to Microcaptive Insurance Companies Did Not Qualify for Tax Deductions

Carlton Fields on

The U.S. Tax Court recently upheld a determination by the IRS that premium payments to certain microcaptives could not be deducted for tax purposes because the premium payments were not actually for “insurance.”...more

Carlton Fields

U.S. Tax Court Finds Captive Insurer Is Not an “Insurance Company” Under the Internal Revenue Code

Carlton Fields on

In this case, Reserve Mechanical Corp. (“Reserve”), a captive insurer incorporated under the laws of Anguilla, sued the Commissioner of Internal Revenue in the U.S. Tax Court regarding the Commissioner’s findings of $477,261...more

Carlton Fields

Tax Court Disallows Deductions For Payments To Captive Insurance Company

Carlton Fields on

A husband and wife who paid $1.54 million in premiums to their captive insurance company and $720,000 in premiums to another insurer over two years, almost all of which ended up back in their bank accounts, have had their tax...more

Holland & Knight LLP

Takeaways from the Tax Court's First Micro-Captive Insurance Ruling

Holland & Knight LLP on

• The U.S. Tax Court recently ruled in Avrahami v. Commissioner, the first litigated Tax Court case involving an 831(b) captive insurance company. • The Tax Court held that two of the key factors that define "insurance"...more

Fox Rothschild LLP

Tax Court Issues Opinion Striking Down Captive Insurance Arrangement

Fox Rothschild LLP on

The Tax Court has issued its long-awaited decision addressing captive insurance arrangements. In Avrahami v. Commissioner, 149 T.C. No. 7 (2017), the Tax Court held that payments made from a number of businesses owned by the...more

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