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U.S. Supreme Court Decision May Pave Way for Future IRS Lawsuits

The U.S. Supreme Court recently rendered a unanimous opinion holding that the Anti-Injunction Act (AIA) did not block a lawsuit brought by CIC Services against the Internal Revenue Service (IRS), delivering an important...more

When IRS Penalty Assertions Are Unlawful

One of the most highly litigated issues in U.S. Tax Court is whether taxpayers are liable for certain penalties, additions to tax or additional amounts (each, a "penalty" and collectively, "penalties"). This should come as no...more

IRS Continues to Audit and Litigate Against Cannabis Businesses

As Congress continues to deliberate the federal legalization of marijuana, the cannabis industry continues to face scrutiny from the IRS under Section 280E of the Internal Revenue Code (Code). Enacted in 1982 in response to a...more

Contract Allocations and Judicial Doctrines

In Cotto-Vázquez v. United States, CIV. NO.: 16-2807 (SCC) (D.P.R. March 11, 2021), Miguel Ángel Cotto-Vázquez (Cotto),1 the former four-time Puerto Rican boxing champion, became involved in another fight. This time he faced...more

When Is a Tax Return "Filed"?

In Notice 2004-45, 2004-2 C.B. 33, the IRS put taxpayers who were asserting to be bona fide residents of the U.S. Virgin Islands (USVI) and who were not following the requirements of meeting the applicable bona fide residency...more

IRS Fishing Expedition Is Successful and Raises Important Attorney-Client Privilege Concerns

The attorney-client privilege is one of the bedrocks of the legal profession. It permits communications between a client and an attorney to remain privileged. The U.S. Supreme Court has stated that by assuring...more

The Reasonable-Basis Defense: Waiver of Attorney-Client Privilege?

This Holland & Knight alert is not focused on the structured trust advantaged repackaged securities (STARS) transaction or the economic substance doctrine, which were the primary issues before the U.S. Court of Appeals for...more

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