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S. Michael Chittenden

Special Counsel

Washington +1 202 662 5295 mchittenden@cov.com Download V-card

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Michael Chittenden practices in the areas of tax and employee benefits with a focus on the Foreign Account Tax Compliance Act (FATCA), information reporting (e.g., Forms 1095, 1096, 1098, 1099, W-2, 1042, and 1042-S) and withholding, payroll taxes, and fringe benefits. Mr. Chittenden advises companies on their obligations under FATCA and assists in the development of comprehensive FATCA and Chapter 3 (nonresident alien reporting and withholding) compliance programs.

Mr. Chittenden advises large employers on their employment tax obligations, including the special FICA and FUTA rules for nonqualified deferred compensation, the successor employer rules, the voluntary correction of employment tax mistakes, and the abatement of late deposit and information reporting penalties. In addition, he has also advised large insurance companies and employers on the Affordable Care Act reporting requirements in Sections 6055 and 6056, and advised clients on the application of section 6050W (Form 1099-K reporting), including its application to third-party payment networks.

Mr. Chittenden counsels clients on mobile workforce issues including state income tax withholding for mobile employees and expatriate and inpatriate taxation and reporting.

Mr. Chittenden is a frequent commentator on information withholding, payroll taxes, and fringe benefits and regularly gives presentations on the compliance burdens for companies.

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Advised a large multinational retailer on the development of a comprehensive Chapter 3 and Chapter 4 (FATCA) compliance program, registration of foreign financial institutions within its expanded affiliated group, and the application of FATCA regulations and intergovernmental agreements to entities and retirement plans located in several foreign countries.
Advised several large insurance companies on Form 1095-B reporting, including TIN solicitation requirements, error correction, identification of the employer sponsoring a group health plan, association plan reporting, VEBA reporting, multiemployer plan reporting, and other aspects of the regulations, and drafted extensive comments for submission to and testified before the IRS and Treasury Department regarding the challenges faced by insurers in soliciting and reporting the TINs of covered individuals.
Represented a large energy company in a multifaceted dispute with the IRS related to numerous alleged information reporting and withholding failures, including the imposition of intentional disregard penalties.
Advised a large financial company on the proper tax treatment of more than 200 different types of earnings and deductions for federal income tax withholding, FICA taxes and Federal Unemployment Tax Act (FUTA) tax purposes, as well as state income tax withholding and state unemployment insurance tax treatment in more than 20 states and numerous counties, school districts and cities.

Advised an auction service provider on the application of Section 6050W reporting to its business with a focus on whether it operates a third-party payment network.
Advised large employers on Form 1095-C and Form 1094-C reporting, including issues related to self-insured coverage, multiemployer plan reporting, reporting for nonemployee directors, retirees, and part-time employees, and TIN solicitation requirements.

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American Bar Association, Section of Taxation
The District of Columbia Bar, Taxation Section

IRS Releases Proposed Regulations on the Mechanics of Income Tax Withholding

Today, the IRS published proposed regulations addressing changes made by the Tax Cuts and Jobs Act of 2017 (the “TCJA”) to how an employee instructs an employer to withhold income taxes on his or her Form W-4 (Employee’s Withholding Certificate). The Form W-4 was redesigned for 2020 to reflect the TCJA changes to how income...… Continue Reading

Justice Department Continues Criminal Prosecutions in Employment Tax Cases

Over the last few years, the Justice Department has worked with the IRS to more aggressively prosecute cases involving employment tax noncompliance and the failure to remit trust fund taxes to the U.S. Treasury. Trust fund taxes are taxes withheld from the wages of employees such as federal income tax withholding and FICA tax withholding. ...… Continue Reading

IRS Launches New Tax Withholding Estimator

Earlier this year, the IRS issued IR-2020-09, in which it announced the launch of a new and improved Tax Withholding Estimator. The Tax Withholding Estimator (the “Estimator”) is designed to help employees adjust their federal income tax withholdings by performing a “Paycheck Checkup.” The process also helps employees target the refund they want by ...

IRS Issues Interim Guidance on Income Tax Withholding from Deferred Income Distributions

The IRS recently released Notice 2020-3, which provides interim guidance on default federal income tax withholding rates applicable to certain periodic payments of deferred income. The Notice also provides clarity as to how the IRS will accommodate a change that affects the form used to elect federal income tax withholding from wages, but not the...… Continue ...

Treasury Finalizes Section 871(m) Regulations and Further Extends Transitory Relief

On December 16, 2019, the Treasury and the IRS released final regulations under section 871(m) of the Internal Revenue Code. The regulations finalize the 2017 temporary and proposed section 871(m) regulations without any substantive change. On the same day, the Treasury and the IRS released Notice 2020-2 to extend through 2022 the relief provided in...… ...

Proposed 162(m) Regulations are a “Lump of Coal”

To corporations hoping for a holiday reprieve from the IRS’s narrow interpretation of the grandfathering rules included in the Tax Cut and Jobs Act (“TCJA”) amendment of section 162(m), the IRS has said “Bah… Humbug!” To those foreign private issuers, publicly traded partnerships, and issuers of public debt hoping for relief from the expanded definition...… ...

Notice 2019-63 Delivers Relief for Providers of Minimum Essential Coverage

Holding true to its holiday tradition, the IRS yet again decided to extend the deadline by which providers of minimum essential coverage (including certain applicable large employers (“ALEs”)) must furnish information statements to individuals regarding their 2019 insurance coverage. However, due to the effective elimination of the ACA’s individual mandate ...

The IRS Introduces More Informative Backup Withholding Notices for Payers

On November 14, 2019, the IRS announced that it has redesigned Notices CP2100 and CP2100A with the goal of providing more information to affected payers. These Notices are used to alert payers that the IRS received Forms 1099 containing incorrect or missing Taxpayer Identification Numbers (TINs) for payees and that the payer may need to contact...… Continue ...

Significant TCJA Guidance Due Before End of Year, Kautter Says

Treasury Assistant Secretary for Tax Policy David Kautter attended the AICPA National Tax Conference on November 13, 2019, and commented that significant TCJA-related guidance should be expected to be released before the end of 2019. Such guidance is likely to include proposed regulations addressing (1) federal income tax withholding under section 3402, (2) the ...

November 15 Deadline Approaching for 2019 Qualified Intermediary Applications

On November 6, the IRS issued its final reminder alert that the deadline for all Qualified Intermediary (“QI”) (including Qualified Derivatives Dealer (“QDD”)), Withholding Foreign Partnership (“WP”) and Withholding Foreign Trust (“WT”) applications for the 2019 year is November 15, 2019. In general, a QI agreement allows a foreign intermediary to simplify its ...

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S. Michael Chittenden

Representative Matters

Memberships and Affiliations

News and Insights (Showing 5 of 12) (Showing 12 of 12)

IRS Releases Proposed Regulations on the Mechanics of Income Tax Withholding

Justice Department Continues Criminal Prosecutions in Employment Tax Cases

IRS Launches New Tax Withholding Estimator

IRS Issues Interim Guidance on Income Tax Withholding from Deferred Income Distributions

Treasury Finalizes Section 871(m) Regulations and Further Extends Transitory Relief

Proposed 162(m) Regulations are a “Lump of Coal”

Notice 2019-63 Delivers Relief for Providers of Minimum Essential Coverage

The IRS Introduces More Informative Backup Withholding Notices for Payers

Significant TCJA Guidance Due Before End of Year, Kautter Says

November 15 Deadline Approaching for 2019 Qualified Intermediary Applications

How A Procedural Misstep Can Invalidate IRS Penalties

Supreme Court Overturns Quill and Broadens Businesses’ Tax Collection Obligations

Accolades

Practices

Industries

Education

Georgetown University Law Center, J.D., 2009

Johns Hopkins University, B.A., 2000

Bar Admissions