Artificial Intelligence continues to impact all industries as companies and individuals try and find the perfect balance between automation and sufficient oversight and monitoring. Tax reporting would appear, on its face, to be a prime candidate for the promises of efficiency achieved through AI’s streamlined review of large amounts of data and identification of potential
On Feb. 19, 2025, President Donald Trump issued Executive Order 14219, titled “Ensuring Lawful Governance and Implementing the President’s ‘Department of Government Efficiency’ Deregulatory Initiative.” The primary purpose of Executive Order 14219 is to direct federal agencies to review and rescind regulations that are deemed unconstitutional or that undermine national interests. The executive order
The Internal Revenue Service was aware of significant underreporting of cryptocurrency on tax returns and used one of its investigative tools (i.e., a John Doe summons) in 2016 to seek financial information on thousands of individuals, including James Harper. Harper sued in 2020, alleging unlawful access to his private financial information, and has been embroiled
The Internal Revenue Service (IRS) recently issued Private Letter Ruling (PLR) 202504006, addressing several important estate and gift tax questions related to the division of a marital trust and the subsequent disclaimer of a surviving spouse’s interest in a portion of the trust. This ruling provides valuable insights into the tax treatment of trust divisions
In 2024, the IRS ramped up its focus on partnerships, including several actions before President Trump took office. However, with a new Treasury Secretary Scott Bessent confirmed, new IRS Commissioner Billy Long named but not yet confirmed, federal funding cuts, a federal hiring freeze, and employee reductions at both IRS and the Department of Justice
Headlines and updates on sweeping changes to operations and staffing with regards to numerous federal agencies, and now implementing new tariffs, as we enter tax filing season may have people even more on edge than years prior at the sight of a letter from the IRS or any chatter about taxes in general. If the
An old German proverb states that “to change and to change for the better are two different things.” As 2024 ends, the legal and business communities who must navigate government scrutiny are seeing the signs of change in the regulatory landscape on the horizon. The pencils for redrawing the lines of government involvement in economic
Monetizing intellectual property (IP) presents complex tax challenges, particularly in determining whether proceeds are taxed at favorable capital gains rates or higher ordinary income rates. Sales of IP assets must transfer substantial rights to qualify for capital gains treatment, while income from licensing agreements is generally taxed as ordinary income. These distinctions require careful transaction
On December 12, 2024, Frank Richard Ahlgren III of Austin, Texas, was sentenced to two years in prison for filing a false tax return, marking the first legal-source cryptocurrency income tax case. The case has garnered attention for its significance in cryptocurrency tax enforcement, as it represents a prosecution based purely on tax issues rather
Federal payroll obligations imposed on employers can be expensive and time-consuming. Therefore, it is not uncommon for companies to outsource these responsibilities to third parties referred to as “third-party payers” (TPPs). Under a TPP arrangement, the TPP deducts, withholds, and remits employment taxes and prepares and files the corresponding employment tax returns on behalf of