Prose by Tax Pros - Another Article by Hale E. Sheppard

The tax press has focused recently on captive insurance, conservation easements, Employee Retention Credits, and other “hot” topics. However, international tax enforcement in general, and big penalties for unfiled FBARs in particular, are still key issues. Several cases, largely unnoticed, have held that the IRS can extend the period for assessing FBAR penalties, even though the initial deadline e...

Battles over Employee Retention Credit (“ERC”) claims are turning more serious now, with many audits, administrative appeals, and cases getting underway. Taxpayers hoping to prevail against the IRS or Department of Justice need to have a deep understanding of legislative, substantive, procedural, and strategic ERC issues. Understandably, loads of taxpayers are having trouble keeping up with evolvi...

Complying with international information-reporting duties is difficult; the rules are complex, dense, and obscure. Things get even more complicated when it comes to people who are residents, for tax purposes, of both the United States and another country. These so-called “dual residents” have special disclosure rules, the violation of which can trigger taxes, penalties, extended assessment periods...

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...

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...

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 a...

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 la...

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 lig...

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 capabiliti...

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 dec...

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...

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 e...

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 inventor...

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...

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...

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 Reten...

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 D...

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...

At some point during most audits, taxpayers will ponder whether, or to what extent, they should “cooperate” with the IRS. They also might ask what, exactly, cooperation means in a particular situation. These are critical questions to which many taxpayers lack clear answers, and this type of unawareness can lead to bad decisions. This article describes duties associated with foreign accounts, stand...

Fighting over when owners of limited partnerships must pay self-employment taxes has lasted nearly five decades. This struggle is attributable to several things, including the absence of applicable regulations, rapid evolution of business entities, and more. Uncertainty has caused taxpayers to claim disparate tax positions and triggered several big-dollar cases. This article, just one in a series,...

The IRS has a limited period to enforce the rules, and taxpayers hope to go unnoticed until that opportunity has passed. Timing issues do not disappear, though, simply because taxpayers get selected for audit or approach the IRS pro-actively. Indeed, they might become more important than ever, because many interactions with the IRS involve extensions of assessment-periods, some voluntary, others c...

The IRS recently launched its second major effort to dispense with cases involving what it calls syndicated conservation easement transactions. In order for partnerships and their partners to make intelligent decisions, they first need to understand the context. This includes the types of challenges the IRS raises in easement disputes, the terms of the initial settlement introduced back in 2020, t...

International tax disputes often create important guidance, some obvious, some not.  Aroeste v. United States is a great example. That case involves the mundane issue of FBAR penalties, but it presents exciting and novel issues, too. It makes noteworthy rulings about whether dual residents can seek FBAR protection from tax treaties, whether late filing of certain information returns prevents taxpa...

Everyone knows that IRS is struggling to timely process and audit Employee Retention Credit (“ERC”) claims. What many people do not realize, though, is that the Tax Court issued a decision in January 2024 that might affect timing issues. This article, another in a series, discusses ERC guidance, the three-year and five-year assessment periods under current law, key Tax Court cases addressing the i...

The IRS is trying various methods to halt what it considers improper Employee Retention Credit (“ERC”) claims, including penalty threats. Browbeating taxpayers with potential penalties is standard stuff, but it becomes particularly interesting in the ERC context, where the IRS’s ability to carry out its warnings is questionable. This article, the latest in a series, describes the evolving ERC guid...