In a case that every tax professional should take note of, the prominent law firm Sidley Austin LLP finds itself defending against claims that it provided faulty tax advice over two decades ago, leading to massive IRS liabilities for a family. The plaintiffs, the Cáceres family, are seeking to recover $7 million after settling with the IRS, claiming Sidley's advice on a complex asset liquidation set them up for disaster. The kicker? The lawsuit was filed over 25 years after the advice was given. So, how are the plaintiffs still able to pursue the case? It all boils down to a claim of fraud—and how that could toll the statute of limitations.

Summer may have ended but the education never does here at Think Outside the Tax Box! Join us this winter for our brand-new series of live webinar events spotlighting an intriguing mix of topics all focused on improving you, your business, and your ability to better serve your clients! All of these live events are included FREE with your Basic or Professional subscription and include Continue Education Credits for those who qualify! Winter time is a great time to be part of the Think Outside the Tax Box community! Here are the details of what we have in store for you…

Yes, the IRS does forgive some tax penalties. The IRS refers to this forgiveness as penalty abatement. Abatement is the act or process of reducing or removing something. In this case it is removing or reducing a penalty. But penalty forgiveness is not a blanket offer that everyone qualifies for the way the radio ads make it seem. There is a process that the IRS has for requesting and granting abatement. It is up to the taxpayer to prove that they qualify for abatement. That’s where you come in.

The story of James J. Maggard has some interesting and possibly valuable lessons. The one that strikes me as particularly important is that it makes it crystal clear that disproportionate distributions contrary to a corporation’s governing documents will not blow its S election. That does not mean that disproportionate distributions are just fine and that you don’t need to address them. There is a practical lesson about being careful who you take on as fellow shareholders. And there is another slightly odd lesson, that almost makes me want to create a new law of tax planning: Don’t deliberately involve the IRS in your business disputes. Their job is not to help you.

Something we never have a shortage of are proposals to change our tax systems. When it’s election time, we hear even more proposals, as well as how various parts of our tax system are flawed, usually due to actions or inactions of the opposing party. We also hear lots of incomplete statements, promises of tax changes too costly to be enacted, and ideas that will be replaced by the time the winner gets down to crafting a real set of tax and budget proposals. This article describes some of the tax proposals of the two presidential candidates along with suggestions on how we should analyze them against principles supporting effective tax systems, with highlights of some important facts seemingly missing from current tax discussions. These proposals are also relevant to members of Congress as to whether they support any of them and how they align with tax changes that the member would like to see enacted.

Much of what happens in Tax Court is run-of-the-mill. Once the tax general practitioner learns the jurisdictional limits and procedural moguls, s/he can advise clients whether to spend the sixty bucks and the certified mail fees when TAS, Examination or Appeals can't deliver an acceptable result. Following the Court's orders and opinions for a while should do that. I try to present the less-than-usual, below-radar points for generalists and specialists.

The IRS has released the updated per diem rates for the 2024-2025 period (IRS Notice 2024-68), which are now effective for business travel beginning October 1, 2024. These rates play an essential role in helping tax professionals and businesses substantiate the ordinary and necessary expenses incurred by employees while traveling for work. Here’s what you need to know about how per diem works, the effective dates of these changes, and a comparison of the new rates with last year’s numbers.

In a recent turn of events that has caught the attention of financial experts and policymakers alike, Senate Finance Committee Chairman Ron Wyden, D-Ore., has unveiled the results of an 18-month investigation into the use of Private Placement Life Insurance (PPLI) by the ultra-wealthy. The investigation, the first of its kind focusing on PPLI, highlights the use of these policies as a significant tax shelter mechanism, revealing the ways in which a small number of wealthy individuals are leveraging them to avoid substantial tax liabilities.