Held Captive: Micro-Captive Insurance in the Aftermath of Avrahami

Jason Freeman Captive Insurance Leave a Comment

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The IRS recently notched a victory in the much-anticipated Tax Court decision of Avrahami v. Commissioner—the first micro-captive insurance decision to go to press.  The court’s 105-page opinion dealt a blow to the micro-captive insurance industry, which has been under increased IRS scrutiny in recent years.  And with several similar cases still in the pipeline, some have questioned whether it …

A Primer on the Tax Implications of Settlements and Judgments

Jason Freeman Uncategorized Leave a Comment

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Your client just settled—or better yet, won a judgment.  What are the tax consequences?  Admittedly, the tax impact of resolving a dispute is often little more than an afterthought.  But a client’s net after-tax recovery can vary drastically depending on the applicable tax rules.  An attorney armed with an understanding of the relevant tax issues has an advantage over opposing …

The Computer Fraud and Abuse Act (CFAA)

Jason Freeman Computer Crimes, Uncategorized Leave a Comment

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The Computer Fraud and Abuse Act (CFAA) criminalizes, among other things, the act of intentionally accessing a computer without authorization.  The CFAA, which is codified at 18 U.S.C. 1030, was originally enacted by Congress in 1986 to combat various forms of “computer crime.”  At that time, this was largely understood to cover “hacking or trespassing into computer systems or data.”  The …

Computer Crimes

Jason Freeman Computer Crimes Leave a Comment

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Cybercrimes continue to be among the fastest growing areas of federal criminal enforcement—and to pose one of the most significant threats to business and personal security.  One need look no further than the seemingly daily news releases of the latest large-scale data breach to recognize that no one is immune to cybercrime.  Estimates indicate that the global cost of cybercrime …

Taxes and Bankruptcy: IRS-Prepared Substitute Returns

Zach Smith Uncategorized Leave a Comment

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A taxpayer filing for bankruptcy with unfiled tax returns faces potential pitfalls. In order to ensure that a debtor’s federal tax liability is discharged in the bankruptcy, the potential bankruptcy debtor must know and comply with the requirements of the circuit where the debtor will file their bankruptcy petition. The recent case of In re Forrester demonstrates several of the …

IRS Penalties—A Brief Primer

Jason Freeman Uncategorized Leave a Comment

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There are currently more than 150 penalties contained in the Internal Revenue Code—a penalty for nearly every conceivable reporting, filing, and payment requirement failure.  While penalties have long been a component of the Federal tax laws, the number of penalties has grown substantially over time.  There are, to put it in perspective, nearly ten times more penalties in the current …

IRS Required to Return FBAR “Penalty:” Penalty was “Illegally Exacted”

Jason Freeman FBAR, Uncategorized Leave a Comment

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The much-anticipated decision in Bedrosian v. United States was released on Wednesday of this week, and it did not fail to disappoint—unless, of course, you find yourself on the latter side of the “v” in the case caption.  The case presented a fundamental FBAR issue: was Bedrosian’s failure to report his foreign account “willful?”  If it was, he would have …

Determining the Enforceability of a Section 6038A Summons

Zach Smith International Tax, Uncategorized Leave a Comment

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When is a section 6038A summons enforceable? The IRS must satisfy certain statutory and other requirements for a section 6038A summons to be enforceable. One approach to challenging a summons is to demonstrate that the IRS did not comply with the Powell requirements – requirements that take their name from the Supreme Court’s seminal case in United States v. Powell, …

The Crime of Tax Evasion

Jason Freeman Tax Fraud, Uncategorized Leave a Comment

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Tax evasion is a phrase that is often used to describe a wide variety of tax-related violations.  In the world of tax administration/enforcement, however, it has a specific statutory meaning.  It has been the charge of choice in a number of high-profile cases throughout history—from the convictions of Al Capone to Leona Helmsley to Wesley Snipes.  With IRS estimates indicating …

Is “Form” “Substance” When it Comes to Law? The Future of the Doctrines of Economic Substance and Substance Over Form

Jason Freeman Economic Substance, Substance over Form, Uncategorized Leave a Comment

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Earlier this year, the Sixth Circuit took aim at the “substance-over-form” doctrine, an amorphous jurisprudential concept that has long shadowed the textually-driven Internal Revenue Code.  See here.  Its opinion is a gem; a forceful rebuke that leads with an attention-grabbing reference to Caligula and raises serious questions about the role (and limits) of the doctrine of substance over form: Caligula …