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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 FAQs Provide Welcome Guidance on Employee Retention Credit and PPP Loans in M&A Transactions

On November 16, the IRS added two new FAQs to its website that address an issue that has been concerning employers since the CARES Act was adopted. For purposes of the employee retention credit (“ERC”), Section 2301(d) of the CARES Act includes an aggregation rule that treats all employers required to be aggregated under section...… Continue Reading

Preamble to Final Regulations on the Mechanics of Income Tax Withholding Provide Transition Method for Pre-2020 Forms W-4

On October 6, the IRS published final 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 based on the employee’s Form W-4 (Employee’s Withholding Certificate). These final regulations were issued only 8 months after the proposed regulations were...… Continue ...

IRS Provides Guidance on Preparation of Forms W-2 for Employees with Deferred Social Security Tax Withholding

On Friday, October 30, the IRS provided guidance regarding the proper reporting on Form W-2 for employers who deferred the withholding of the employee share of Social Security tax under Notice 2020-65. (See earlier coverage.) Based on the IRS guidance, employers should report FICA wages up to the OASDI (Social Security) wage base in Box...… Continue Reading

New D.C. Transportation Benefits Law Creates Potentially Bumpy Road for Employer Compliance

Soon, many District of Columbia employers will be subject to a new “parking cash-out” law designed to promote environmentally friendly commuting options, i.e., other than individual commutes by automobile. At a high-level, parking cash-out laws generally require employers that provide free or subsidized parking to offer to pay employees cash in lieu of the ...

IRS Updates Guidance on Qualified Plan Distributions to State Unclaimed Property Funds

The IRS recently published new guidance on the tax withholding and reporting consequences associated with qualified retirement plan distributions to state unclaimed property funds. In Revenue Ruling 2020-24, the IRS clarified that distributions from qualified retirement plans to state unclaimed property funds are subject to both federal income tax withholding ...

Bad News for New York Nonresident Telecommuters: New York Issues COVID-19 Telecommuting Guidance

Without notice or fanfare, the New York Department of Taxation updated guidance on its website to address the application of its “convenience of the employer” rule to COVID-19 telecommuters. The question of whether New York would consider employees who are working remotely due to the pandemic as doing so for “convenience” or “necessity,” has been...… Continue ...

New Hampshire Brings COVID-19 Tax Dispute to Supreme Court; Case Highlights Challenges Facing Employers and Employees

On Monday, October 19, the State of New Hampshire filed a bill of complaint in the Supreme Court of the United States asserting that its southern neighbor, Massachusetts, is violating its state sovereignty. The suit attacks Massachusetts’s emergency regulations governing the taxation of income during the COVID-19 state of emergency. Massachusetts enacted a rule ...

Final Regulations Address TCJA Disallowance for Meal and Entertainment Expenses

On October 9, the IRS published final Treasury Regulations addressing the deduction disallowance of expenses associated with providing entertainment, business meals, and other food and beverages in the Federal Register. The final regulations, which track the proposed regulations published on February 26, 2020, preserve, with certain limitations, taxpayers’ ...

IRS Posts Tax Tip on Backup Withholding

On October 14, 2020, the IRS posted Tax Tip 2020-136 entitled, “Helpful information for taxpayers on backup withholding.” This particular Tax Tip serves as a great reminder for payers making payments for which backup withholding is required, especially if they are unaware of the troubling consequences of noncompliance. Backup withholding is imposed at a ...

OASDI (Social Security) Wage Base Up Over 3.7% for 2021

On October 13, the Social Security Administration announced that the Old Age, Survivors, and Disability Insurance (“OASDI”) wage base will increase to $142,800 for 2021. The 3.7% increase follows a 3.6% increase in the wage base for 2020 and a 3.5% increase for 2019. Wages in excess of the wage base paid by an employer...… Continue Reading

Summary of Tax Provisions in the Coronavirus Aid, Relief, and Economic Security ("CARES") Act

Late last night, the Senate passed (96-0) the Coronavirus Aid, Relief, and Economic Security ("CARES") Act that was introduced by several Senate Republicans last Thursday. This follows a number of days of whirlwind negotiations, beginning with the Senate where, on Sunday night, a procedural vote failed to garner the 60 votes necessary to move the legislation ...

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S. Michael Chittenden

Representative Matters

Memberships and Affiliations

News and Insights (Showing 5 of 14) (Showing 14 of 14)

IRS FAQs Provide Welcome Guidance on Employee Retention Credit and PPP Loans in M&A Transactions

Preamble to Final Regulations on the Mechanics of Income Tax Withholding Provide Transition Method for Pre-2020 Forms W-4

IRS Provides Guidance on Preparation of Forms W-2 for Employees with Deferred Social Security Tax Withholding

New D.C. Transportation Benefits Law Creates Potentially Bumpy Road for Employer Compliance

IRS Updates Guidance on Qualified Plan Distributions to State Unclaimed Property Funds

Bad News for New York Nonresident Telecommuters: New York Issues COVID-19 Telecommuting Guidance

New Hampshire Brings COVID-19 Tax Dispute to Supreme Court; Case Highlights Challenges Facing Employers and Employees

Final Regulations Address TCJA Disallowance for Meal and Entertainment Expenses

IRS Posts Tax Tip on Backup Withholding

OASDI (Social Security) Wage Base Up Over 3.7% for 2021

The Curious Case of New Jersey and Ms. Darcey: New Jersey Taxation of Nonqualified Deferred Compensation

Summary of Tax Provisions in the Coronavirus Aid, Relief, and Economic Security ("CARES") Act

How A Procedural Misstep Can Invalidate IRS Penalties

Supreme Court Overturns Quill and Broadens Businesses’ Tax Collection Obligations

Accolades

COVID-19: Legal and Business Toolkit

Practices

Industries

Education

Georgetown University Law Center, J.D., 2009

Johns Hopkins University, B.A., 2000

Bar Admissions