If you ask someone a direct question and the person responds with incorrect information, is the person bound by their misrepresentation? This raises questions of “estoppel,” which apply to most litigants. But does it apply to IRS employees who make a misrepresentation? Put another way, can you rely on statements by IRS representatives? The court…
Tax Articles
The Late Mark-to-Market Election
Those who trade stocks can take advantage of the mark-to-market election to convert capital losses into ordinary losses. This election is only available to “traders.” There are often questions as to when a taxpayers trading activities are sufficient to warrant being treated as a “trader” for tax purposes. By the time the taxpayer discovers that…
Substantial Authority, When the Authority is Not Clear
What if you have a tax question and find a court case that: (1) has the same facts as your case, (2) addresses the same tax item as in your case (such as a tax deduction, credit, etc.), and (3) the court case is decided in the taxpayer’s favor, but the court case does not…
About Tax Preparer Penalty Audits
The IRS’s power to regulate tax return preparers was limited by the Loving v. Internal Revenue Service, 742 F.3d 1013 (D.C. Cir. 2014) line of cases. These cases generally limit the IRS’s ability to regulate tax preparer conduct at an administrative level. But the IRS still has a number of tools at its disposal to…
Tax Loss Planning: The At-Risk Rules
Are you purchasing a business or real estate that involves financing a business or investment that is likely to produce tax losses in the future? Or have you already made the purchase? If so, there may be ways to ensure that you can take the loss in the future. To do so, you have to…
When Clients Testify Against Their Tax Preparer
The IRS has been focusing on examinations of tax return preparers. These examinations often result in the imposition of civil penalties under Section 6694 and 6695. But they can also result in criminal liability for the tax return preparer. The criminal sentencing guidelines can be problematic for tax return preparers. The Keleta v. United States,…
Fix to Duplicate IRS Address Problem
The IRS sends taxpayers letters and notices from quite a few different IRS offices. As a result, taxpayers are often confused as to what IRS office to respond to. This is particularly true if the IRS letter or notice includes more than one IRS address. The IRS has maintained a harsh stance on taxpayers who…
The Mailbox Rule Extends Time to Recoup Tax Refund
Taxpayers often miss tax filing deadlines. This is even true when the IRS owes the taxpayer money back. Taxpayers have a limited time to request a refund of overpayments. The recent Harrison v. Commissioner, No. 3:19-cv-00194 (2nd Cir. 2020) case provides an opportunity to consider these rules–particularly the mailbox rule. Contents1 Facts & Procedural History2…
Can “Business Synergies” be an Asset that Increases a Tax Loss?
The tax consequence of a transaction often depends on how one characterizes or describes the transaction. Business synergies are often cited as the rationale for merger and acquisition deals. In a M&A deal, are “business synergies” a separate asset for tax purposes? Can you list “business synergies” as a separate asset and then take a…
Timing for Written IRS Manager Approval for Penalties
The courts recently held that penalties have to be abated if the IRS does not obtain written manager approval for the penalties. The IRS has been abating penalties for this since the ruling. But there is a question as to when does the IRS have to obtain manager approval? Is it sufficient that the IRS…