Tax Court Allows Rollover Contribution Past Deadline

Income Tax, Tax, Tax Controversy

In a recent Memorandum opinion issued by the Tax Court, the Court held that the 60-day time limit for individual retirement account (“IRA”) rollovers was met for a distribution and subsequent recontribution of IRA funds despite the funds not being credited back to the IRA upon recontribution until 62 days after the initial distribution. The IRS…
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IRS Audits: Why Me and What to Expect

Income Tax, Tax, Tax Controversy

Introduction This article is the first article in a multi-part series of articles that I will be doing on IRS audits. The purpose of this series is to demystify the audit process, inform readers about how audits are conducted, and provide readers with an understanding of what to expect if selected for examination. This article…
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Collection Actions Invalidated for Failure to Follow Required Procedures

Tax, Tax Controversy

The Tax Court recently issued decisions in Kearse v. Commissionerand Commission v. Romano-Murphy (“Romano-Murphy II“). Both cases involved review of administrative determinations made by IRS appeals officers in collections due process (“CDP”) proceedings. Section 6330(c)(1) requires appeals officers conducting CDP hearings to verify that the requirements of any applicable law or administrative procedure related to the assessment…
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Sixth Circuit Clarifies Substance Over Form Doctrine in “MidCo” Case

Business Transactions, Income Tax, Tax, Tax Controversy

After the Summa Holdings case, the substance over form doctrine was left with a significant black eye by the Sixth Circuit. On May 15, 2019, the Sixth Circuit, upheld a transferee liability claim against shareholders of a Tennessee corporation while also clarifying its holding is Summa Holdings. While the Summa Holdings discussion is certainly interesting, the…
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Tax Court Acknowledges Remote Material Participation

Income Tax, Tax, Tax Controversy, TCJA

Can the material participation tests of Section 469 be met remotely? The Tax Court says yes. In a recent Memorandum Opinion, the Tax Court (the “Court”) held that Fred Barbara (“Barbara”) satisfied the requirements for materially participating in his Chicago based business despite living in Florida approximately 60% of the year. The Internal Revenue Service (the…
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When Your Captive Is Not In the Insurance Business

Income Tax, Tax, Tax Controversy

In a recent Tax Court Memorandum opinion, the Tax Court (the “Court”) held that a microcaptive insurance arrangement did not meet the requirements to be classified as insurance for federal income tax purposes, and thus upheld the Internal Revenue Service’s (the “IRS”) Notice of Deficiency (the “Notice”) against the company and its related taxpayers who…
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Cavanaugh – Deduction Denied for CEO Misconduct Settlement Payments

Income Tax, Tax Controversy

In Cavanaugh v. Commissioner, the Fifth Circuit Court of Appeals addressed the deductibility of settlement payments made by a corporation to avoid liability arising from the misconduct of a shareholder-employee. Affirming the Tax Court ruling from 2012, the Fifth Circuit held that the settlement payments at issue in Cavanaugh were not deductible under IRC § 162(a) because the…
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