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McDermott’s Real-Time Tax Disputes Insights
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IRS Appeals Will Not Consider Regulatory Invalidity and Subregulatory Procedural Invalidity Challenges

by and | Sep 21, 2022 | , , , , ,

In Mayo Found. for Med. Educ. & Rsch. v. United States, 131 S.Ct. 704 (2011), the Supreme Court of the United States made clear that administrative law rules apply to tax guidance like they do to other federal agency guidance. Since Mayo, the Supreme Court and other courts have provided further guidance—both in the tax and non-tax contexts—regarding the proper analysis in determining the validity of, and deference to, regulatory guidance.

Over the past decade, the number of taxpayer challenges to guidance issued by the Internal Revenue Service (IRS), whether in the form of regulations or subregulatory guidance (i.e., revenue rulings, revenue procedures, notices and announcements), has increased significantly. These challenges have taken a variety of forms, such as regulatory invalidity under Chevron USA, Inc. v. NRDC, 467 U.S. 837 (1984) and procedural invalidity under the Administrative Procedure Act (APA). Some successful challenges to the validity of IRS guidance and the ability to challenge such guidance in a pre-enforcement context include CIC Servs., LLC v. IRS, 141 S.Ct. 1582 (2021); United States v. Home Concrete & Supply, LLC, 132 S.Ct. 1836 (2012); Mann Construction, Inc. v. Commissioner, 27 F. 4th 1138 (6th Cir. 2022); Good Fortune Shipping SA v. Commissioner, 897 F.3d 256 (2018) and Liberty Global, Inc. v. United States, No. 1:20-cv-03501-RBJ (D. Colo. 2022). Many other challenges are pending both at the administrative level and in court.

The IRS and the US Department of the Treasury (Treasury) have noticed the increase in challenges to its published guidance. One important change is the more detailed discussions in preambles to final regulations regarding comments received and how the IRS views and incorporates said comments. This is a welcome development, although sometimes a tortuous one for taxpayers who must wade through hundreds of pages of preambles in some regulation packages. Another change, and the subject of this post, is the IRS’s views on how to deal with such challenges during the administrative process.

A federal tax controversy can involve three levels of review: Examination, Appeals and litigation. At the Examination stage, revenue agents and other IRS personnel develop the facts and determine whether an adjustment is warranted. Importantly, “hazards of litigation” are not considered at the Examination level, meaning, issues are viewed as binary—in favor of the IRS or the taxpayer—and not negotiated as a percentage of the item. However, at the Appeals level, the Appeals team weighs “hazards of litigation” to determine whether a case can be settled by the parties. Hazards of litigation are also considered at the litigation level.

Validly promulgated tax regulations are approved at the highest levels of the IRS, Treasury generally carry the force and effect of law and are binding on taxpayers and the IRS. Subregulatory guidance is also approved at senior levels of the IRS and the Treasury. At the Examination level, the IRS will not entertain challenges to the validity of [...]

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Weekly IRS Roundup February 25 – March 1, 2019

by | Mar 4, 2019 | , ,

Presented below is our summary of significant Internal Revenue Service (IRS) guidance and relevant tax matters for the week of February 25 – March 1, 2019.

February 25, 2019: The IRS issued Revenue Ruling 2019-05, announcing the interest rates for underpayments and overpayments under section 6621 of the Code, applicable for the calendar quarter beginning April 1, 2019.

February 26, 2019: The IRS issued a news release as part of its new Tax Time Guide series, providing information and online resources to help taxpayers understand the changes made by the Tax Cuts and Jobs Act.

February 27, 2019: The IRS released final regulations amending the utility allowance regulations concerning the low-income housing credit under section 42 of the Code.

February 27, 2019: The IRS issued a news release reminding taxpayers who owe federal taxes about potential restrictions on their ability to obtain or renew passports.

February 27, 2019: The IRS scheduled a public hearing for March 14, 2019, on the proposed regulations implementing the Tax Cuts and Jobs Act as it relates to the foreign tax credit.

February 28, 2019: The IRS issued Notice 2019-17, providing relief from underpayment penalties to farmers and fishermen in certain circumstances.

February 28, 2019: The IRS issued a news release as part of its new Tax Time Guide series, providing information and online resources to taxpayers about how to check refund status or pay additional tax owed.

March 1, 2019: The IRS released its weekly list of written determinations (e.g., Private Letter Rulings, Technical Advice Memorandums and Chief Counsel Advice).

Special thanks to Le Chen in our DC office for this week’s roundup.



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Weekly IRS Roundup January 14 – 18, 2019

by | Jan 22, 2019 | , ,

Presented below is our summary of significant Internal Revenue Service (IRS) guidance and relevant tax matters for the week of January 14 – 18, 2019.

January 15, 2019: The IRS issued final regulations implementing the transition tax under section 965 of the Code, enacted as part of the Tax Cuts and Jobs Act.

January 15, 2019: The IRS released an updated contingency plan describing its actions and activities in light of the partial federal government shutdown.

January 16, 2019: The IRS released Notice 2019-11, providing a penalty waiver, under certain conditions, for an individual taxpayer’s underpayment of withholding and estimated income tax, in light of the major changes made by the Tax Cuts and Jobs Act.

January 18, 2019: The IRS issued final regulations providing guidance on the deduction for qualified business income under section 199A of the Code, enacted as part of the Tax Cuts and Jobs Act.

January 18, 2019: The IRS released proposed regulations dealing with previously suspended losses and ownership interests in certain entities for purposes of calculating the deduction under section 199A of the Code, enacted as part of the Tax Cuts and Jobs Act.

January 18, 2019: The IRS released Revenue Procedure 2019-11, providing methods for calculating W-2 wages for purposes of the deduction under section 199A of the Code, enacted as part of the Tax Cuts and Jobs Act.

January 18, 2019: The IRS released Notice 2019-07, proposing a safe harbor for rental real estate enterprises for purposes of the deduction under section 199A of the Code, enacted as part of the Tax Cuts and Jobs Act.

Special thanks to Le Chen in our DC office for this week’s roundup.



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Weekly IRS Roundup July 9 – 13, 2018

by | Jul 16, 2018 | ,

Presented below is our weekly roundup for July 9 – 13, 2018 on significant IRS matters.

July 9, 2018: The IRS released Internal Revenue Bulletin No. 2018-28 including: Notice 2018-48 (lists the population census tracts designated as qualified opportunity zones); Notice 2018-59 (provides two methods for taxpayers to begin construction for the investment tax credit under Section 48); Announcement 2018-11 (Office of Professional Responsibility [OPR] announces recent disciplinary sanctions); Rev. Rul. 2018-20 (rendering obsolete several previous revenue rulings); and Rev. Proc. 2018-35 (modifying Rev. Proc. 2018-31 regarding accounting methods for citrus plant replanting costs).

July 11, 2018: The IRS issued final regulations (T.D. 9834) addressing inversion transactions structured to avoid the purposes of sections 7874 and 367 and other post-inversion tax avoidance transactions.

July 13, 2018: The IRS issued proposed regulations (REG-103474-18) related to the Code section 6695(g) return preparer penalty amending previous guidance to reflect changes made by 2017 federal tax reform.

July 13, 2018: The IRS released it weekly list of written determination (e.g., Private Letter Rulings, Technical Advice Memorandum and Chief Counsel Advice).

Special thanks to Christy Vouri-Misso and Greg Berson in our DC office for this week’s roundup.



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The Slow Death of the Section 385 Regulations

by and | Nov 9, 2017 | ,

Internal Revenue Code (Code) Section 385 provides that the US Department of the Treasury (Treasury) is authorized to issue regulations to determine whether an interest in a corporation is to be treated for purposes of the Code as stock or indebtedness. After decades of inaction, proposed regulations were issued on April 14, 2016. The proposed regulations were not well-received; the tax bar had serious and substantial comments to the proposed regulations. Among the most important critiques, there were criticisms for the potential overbreadth of the regulations’ application to foreign-to-foreign transactions, the lack of a de minimis exception for smaller companies and for the anticipated burden of the contemporaneous documentation requirements.

Treasury released final regulations under Code Section 385, which are effective as of October 21, 2016. Although the proposed regulations were changed in some respects, the final regulations retained strict documentation requirements.

In Executive Order 13789, the President called on Treasury to identify and reduce tax regulatory burdens that impose undue financial burdens on US taxpayers, or otherwise add undue complexity to federal tax law. In response, Treasury indicated on October 2, 2017, that it would potentially revoke the documentation requirements under the proposed regulations. (more…)



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