Prose by Tax Pros

Enforcement actions by the IRS against alleged promoters of abusive transactions and the taxpayers who participate in them are firmly linked. Therefore, defending effectively against IRS challenges requires an understanding of the overlapping rules, standards, and procedures. This article explains unique aspects of so-called promoter penalties, various actions the IRS takes in connection with promoters, effects of such IRS measures on taxpayers who engaged in the transactions under scrutiny, recent events suggesting that promoter investigations might surge, and thoughts about the best path forward in the current environment. Read the full article here. About Hale E. Sheppard HALE E. SHEPPARD, Esq. (B.S., M.A., J.D., LL.M., LL.M.T.)  is a partner at Eversheds Sutherland.  He defends clients in tax audits, tax appeals, and Tax Court litigation, covering both domestic and international issues.

Companies treat some workers as independent contractors, and the IRS insists that they are really employees. This is an old story, one that often triggers disputes. The IRS generally has many procedural advantages when it comes to tax disputes, but companies have a unique tool when it comes to worker-classification fights. This obscure instrument is called “Section 530.” Used correctly, it can result in companies avoiding employment taxes and penalties for past years, while retaining the ability to treat workers as independent contractors in future years. This article, which builds on several others by the author, explains the existing authorities regarding Section 530 and then analyzes the newest guidance from the IRS in 2025. Read the full article here. About Hale E. Sheppard HALE E. SHEPPARD, Esq. (B.S., M.A., J.D., LL.M., LL.M.T.)  is a partner at Eversheds Sutherland.  He defends clients in tax audits, tax appeals, and Tax Court litigation, covering both domestic and inte...

  Ambiguity about when distributions to “limited partners” are exempt from self-employment taxes has existed for five decades. This vagueness has led to many disputes, including numerous cases now winding their way through the courts. The Tax Court has made some significant rulings already, but many of the key issues are far from resolved. This article, the latest in a series, summarizes the relevant law and regulations, describes the only precedential case on the books for many years, explains the Compliance Campaign launched by the IRS, analyzes three recent Tax Court decisions, and identifies several additional cases on the way. Read the full article here. About Hale E. Sheppard HALE E. SHEPPARD, Esq. (B.S., M.A., J.D., LL.M., LL.M.T.)  is a partner at Eversheds Sutherland.  He defends clients in tax audits, tax appeals, and Tax Court litigation, covering both domestic and international issues.

Justified or not, some members of Congress and the IRS are passionate about eliminating tax benefits associated with Private Placement Life Insurance (“PPLI”). The problem, according to those urging a legislative change, is that only certain taxpayers are financially able to access PPLI and this limitation somehow undermines the congressional purpose for offering insurance-related tax inducements. This article, which builds on an earlier one, explains the main benefits of PPLI, chronicles major events over the past decade, and examines the draft legislation that has the potential to upend present treatment of PPLI. Read the full article here. About Hale E. Sheppard HALE E. SHEPPARD, Esq. (B.S., M.A., J.D., LL.M., LL.M.T.)  is a partner at Eversheds Sutherland.  He defends clients in tax audits, tax appeals, and Tax Court litigation, covering both domestic and international issues.

Five years have passed since Congress introduced the Employee Retention Credit (“ERC”) in 2020, a remarkably long list of things have happened since then, and most people have trouble keeping up.   Failure to understand the four ERC laws, evolving IRS guidance, court cases, and related matters could result in financial tragedy for many companies.   Mindful of this reality, this article, which builds on more than two dozen others by the same author, provides legislative background and then explores 40 important events that have occurred during the first half-decade. Read the full article here. About Hale E. Sheppard HALE E. SHEPPARD, Esq. (B.S., M.A., J.D., LL.M., LL.M.T.)  is a partner at Eversheds Sutherland.  He defends clients in tax audits, tax appeals, and Tax Court litigation, covering both domestic and international issues.

When people think about tax enforcement, they rarely consider the IRS attacking payroll companies based on benefits they claimed for their clients, but this is happening with the Employee Retention Credit (“ERC”). What makes this more interesting is that the IRS is attacking both payroll companies and their clients thanks to their joint liability in certain situations. This reality sets the stage for primary battles against the IRS, accompanied by secondary clashes between payroll companies and their clients. The finger pointing has already started, and it will no doubt intensify as ERC enforcement escalates. This article analyzes four recent sources of IRS guidance about which parties will be on the hook when ERC claims get disallowed. Read the full article here. About Hale E. Sheppard HALE E. SHEPPARD, Esq. (B.S., M.A., J.D., LL.M., LL.M.T.)  is a partner in the Tax Controversy Section of Chamberlain Hrdlicka.  He defends clients in tax audits, tax appeals, and Tax Court lit...

Congress introduced the Employee Retention Credit (“ERC”) more than four years ago, but serious enforcement actions are just now getting underway. The IRS, as one part of its comprehensive strategy, has been implementing a multi-step plan designed to convince taxpayers to willingly return ERC payments that they did not deserve in the first place. This article, the latest in a series, analyzes the evolution of ERC benefits by Congress, the no-win situation facing the IRS initially, and some of the steps taken that the IRS has taken thus far to reduce the number of taxpayers it must pursue, including the introduction of its second voluntary disclosure program. Read the full article here. About Hale E. Sheppard HALE E. SHEPPARD, Esq. (B.S., M.A., J.D., LL.M., LL.M.T.)  is a partner in the Tax Controversy Section of Chamberlain Hrdlicka.  He defends clients in tax audits, tax appeals, and Tax Court litigation, covering both domestic and international issues.

Taxpayers who engage in tax fraud face serious consequences, including steep penalties, endless assessment-periods, prolonged trials, reputational damage, and more. Mere allegations of fraud by the IRS can trigger these types of damaging outcomes. Cynics often argue that this is precisely the reason the IRS sometimes claims that fraud occurred in the first place. Fortunately for taxpayers, while alleging fraud is relatively easy, proving it can be hard for the IRS. Two recent Tax Court cases, analyzed in this article, demonstrate this reality. Read the full article here. About Hale E. Sheppard HALE E. SHEPPARD, Esq. (B.S., M.A., J.D., LL.M., LL.M.T.)  is a partner in the Tax Controversy Section of Chamberlain Hrdlicka.  He defends clients in tax audits, tax appeals, and Tax Court litigation, covering both domestic and international issues.

Things constantly evolve when it comes to U.S. tax and information-reporting duties for foreign trusts. A major challenge for taxpayers is keeping up with all the changes because they derive from different sources, in different contexts, at different times. In an effort to clarify and update matters, this article offers a summary of foreign trust rules, followed by a chronological review of the latest enforcement actions, relief measures, cases, regulations, and more. Read the full article here. About Hale E. Sheppard HALE E. SHEPPARD, Esq. (B.S., M.A., J.D., LL.M., LL.M.T.)  is a partner in the Tax Controversy Section of Chamberlain Hrdlicka.  He defends clients in tax audits, tax appeals, and Tax Court litigation, covering both domestic and international issues.

Are taxpayers who acquire Private Placement Life Insurance (“PPLI”) doing something wrong? Certain politicians and academics think so. They argue that taxpayers who have the financial ability to purchase PPLI are somehow “abusing” the system. This article explains the general tax rules favoring life insurance policyholders and their beneficiaries, recent reports and cases putting PPLI in a bad light, and three recent proposals urging legislative changes by Congress and/or increased enforcement by the Internal Revenue Service. Read the full article here. About Hale E. Sheppard HALE E. SHEPPARD, Esq. (B.S., M.A., J.D., LL.M., LL.M.T.)  is a partner in the Tax Controversy Section of Chamberlain Hrdlicka.  He defends clients in tax audits, tax appeals, and Tax Court litigation, covering both domestic and international issues.

Congress instructed the IRS to publish guidance on specific, limited issues related to the Employee Retention Credit (“ERC”). The IRS did so, first issuing regulations about its ability to recapture “erroneous refunds,” followed by additional regulations about its authority to grab related interest payments. These new rules, if they withstand scrutiny, will enhance the IRS’s enforcement capabilities. This article, the latest in a long series, explores four major ERC laws, two sets of regulations recently introduced by the IRS, various assessment periods applicable to ERC claims, and how they all interrelate.  Read the full article here. About Hale E. Sheppard HALE E. SHEPPARD, Esq. (B.S., M.A., J.D., LL.M., LL.M.T.)  is a partner in the Tax Controversy Section of Chamberlain Hrdlicka.  He defends clients in tax audits, tax appeals, and Tax Court litigation, covering both domestic and international issues.

Enforcement actions regarding Employee Retention Credit (“ERC”) claims are on the uptick. An important question is how long the IRS and the Department of Justice have to carry out their missions. The normal rules on timing are straightforward, but things get complicated when one considers exceptions, special rules for particular quarters, potential changes contemplated by Congress, and a novel decision by a Court of Appeals that has received little attention. This article, the latest in a long series on ERC issues, explores the key timing issues, old and new, in the context of ERC disputes. Read the full article here. About Hale E. Sheppard HALE E. SHEPPARD, Esq. (B.S., M.A., J.D., LL.M., LL.M.T.)  is a partner in the Tax Controversy Section of Chamberlain Hrdlicka.  He defends clients in tax audits, tax appeals, and Tax Court litigation, covering both domestic and international issues.

  Many taxpayers parting ways with the United States must file Form 8854 (Initial and Annual Expatriation Statement). Failure to do so is problematic because it can expose taxpayers to the notorious “exit tax.” Few people have seemed to notice, but significant changes might be on the way. This article analyzes worldwide obligations of U.S. individual taxpayers, exit taxes, foundations for Form 8854 filing duties, legislative proposals for increased enforcement, a recent case invalidating the IRS document that introduced Form 8854, and IRS actions in other contexts where the courts have shot down administrative guidance. Read the full article here. About Hale E. Sheppard HALE E. SHEPPARD, Esq. (B.S., M.A., J.D., LL.M., LL.M.T.)  is a partner in the Tax Controversy Section of Chamberlain Hrdlicka.  He defends clients in tax audits, tax appeals, and Tax Court litigation, covering both domestic and international issues.

The IRS tries to gather as much information and documentation as possible when conducting an audit. It attempts to get the data directly from the taxpayer, but it often turns to other sources, too. This is called making third-party contacts. The IRS has been criticized over the years for giving insufficient warnings to taxpayers before starting third-party contacts, and Congress took notice. It enacted a law creating safeguards against inappropriate third-party contacts and later strengthened it. Now, the IRS has issued proposed regulations that severely undercut historical taxpayer protections. This article analyzes the filing and record-keeping duties of taxpayers, information-gathering tools of the IRS, and changes in protections for taxpayers and third-parties over the years. Read the full article here. About Hale E. Sheppard HALE E. SHEPPARD, Esq. (B.S., M.A., J.D., LL.M., LL.M.T.)  is a partner in the Tax Controversy Section of Chamberlain Hrdlicka.  He defends clients ...

Conservation easement disputes have lasted nearly a decade and the end is far for clear. What is apparent, though, is that the IRS is now eager conclude as many cases as possible, and fast. Why? The IRS might be concerned about losing a major case on valuation issues, which could unleash many taxpayer victories in later cases. Another possibility is that the IRS wants to clear its massive inventory of existing SCET cases. Yet another motive might be that battling sophisticated taxpayers in high-dollar, complex, document-intensive cases takes a serious toll on the IRS. The true reasons for the IRS’s desire to resolve conservation easement cases now is not particularly important; what matters is understanding the relevant settlement programs and their nuances. This article, which expands on several of my earlier ones, compares and contrasts three different IRS programs. Read the full article here. About Hale E. Sheppard HALE E. SHEPPARD, Esq. (B.S., M.A., J.D., LL.M., LL.M.T.)  is a ...

  What began as an initiative to help businesses keep workers on the payroll during the COVID crisis has become a quagmire. The processing of new employee retention credit (“ERC”) claims is on hold, guidance is often dense and retroactive, legislation is in limbo, and audits and investigations are starting in earnest. Convinced that billions of dollars in ERC claims were improper, the government has initiated several actions. This article, another in a long series by the author, explores recent administrative, legislative and executive actions to address ERC issues. Read the full article here. About Hale E. Sheppard HALE E. SHEPPARD, Esq. (B.S., M.A., J.D., LL.M., LL.M.T.)  is a partner in the Tax Controversy Section of Chamberlain Hrdlicka.  He defends clients in tax audits, tax appeals, and Tax Court litigation, covering both domestic and international issues.

Most people are somewhat confused about Employee Retention Credit (“ERC”) issues. This is logical given the massive amount of information, much of it inaccurate, released by various sources over the past four years. Among the aspects that escape most people are the enforcement actions taken by the IRS. Understanding these is critical because taxpayers and other parties that might end up in the IRS’s crosshairs cannot effectively defend themselves if they do not know what their adversary is doing. This article, another in a long series, explores the major enforcement tactics used by the IRS thus far in challenging what it considers improper ERC claims. Read the full article here. About Hale E. Sheppard HALE E. SHEPPARD, Esq. (B.S., M.A., J.D., LL.M., LL.M.T.)  is a partner in the Tax Controversy Section of Chamberlain Hrdlicka.  He defends clients in tax audits, tax appeals, and Tax Court litigation, covering both domestic and international issues.

  Employers generally are required to withhold, deposit, and remit taxes on wages paid to their employees. They are obligated to file various returns with the IRS documenting their actions, too. Many employers hire a third-party payer (“TPP”) to handle these duties. Things often go smoothly, but issues can arise when situations get complicated. One example is when an employer files an Employee Retention Credit (“ERC”) claim through its TPP, the IRS allows it, and then it starts looking for persons to audit. This article, the latest in a long series, explains the various ERC laws and analyzes the four main sources of IRS guidance thus far about liability for tax underpayments and penalties resulting from improper ERC claims. Read the full article here. About Hale E. Sheppard HALE E. SHEPPARD, Esq. (B.S., M.A., J.D., LL.M., LL.M.T.)  is a partner in the Tax Controversy Section of Chamberlain Hrdlicka.  He defends clients in tax audits, tax appeals, and Tax Court litigation,...

The IRS has focused on several different transactions in recent years, but its indignation now centers on certain positions taken by taxpayers in connection with Charitable Remainder Annuity Trusts (“CRATs”). This article describes a growing list of IRS efforts to stop what it deems abusive transactions involving CRATs. These include a legal memo, an injunction lawsuit, two Tax Court battles, a Dirty Dozen listing, and, most recently, regulations proposing to categorize items as “listed transactions.” Read the full article here. About Hale E. Sheppard HALE E. SHEPPARD, Esq. (B.S., M.A., J.D., LL.M., LL.M.T.)  is a partner in the Tax Controversy Section of Chamberlain Hrdlicka.  He defends clients in tax audits, tax appeals, and Tax Court litigation, covering both domestic and international issues.

In its effort to win conservation easement cases, the IRS has trotted out lots of different arguments over the years. Some were rejected by the Tax Court upon arrival, others gradually disappeared as taxpayers improved pre-donation documentation to avoid “technical” flaws, and a few still exist. One of the lingering challenges centers on the character of the property on which an easement is placed. This argument has been dubbed the “inventory issue,” and the IRS is now raising it frequently. These efforts have resulted in three recent Tax Court victories for the IRS. This article examines concepts in easement disputes, key participants, legal support for the “inventory issue,” and three pivotal cases thus far. Read the full article here. About Hale E. Sheppard HALE E. SHEPPARD, Esq. (B.S., M.A., J.D., LL.M., LL.M.T.)  is a partner in the Tax Controversy Section of Chamberlain Hrdlicka.  He defends clients in tax audits, tax appeals, and Tax Court litigation, covering both dome...