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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 Issues Notice 2020-65 Providing Guidance on Employee Social Security Tax Deferral

Late Friday, the IRS released Notice 2020-65 providing guidance to employers regarding the implementation of President Trump’s presidential memorandum issued on August 8, 2020. The memorandum directed the Secretary of the Treasury to defer the withholding, deposit, and payment of employee Social Security taxes for the period from September 1 to December 31, ...

IRS Warns Employers Claiming New Tax Credits of Erroneous Penalty Notices

The IRS recently announced that it erroneously sent failure-to-deposit (“FTD”) penalty notices to certain employers that reduced their employment tax deposits on Form 941 (Employer’s Quarterly Federal Tax Return) in anticipation of claiming sick and family leave credits under the Families First Coronavirus Response Act (“FFCRA”) or the employee retention credit ...

IRS Warns Employers to Choose Carefully When Selecting a Payroll Service Provider

On August 19, 2020, the IRS urged employers to exercise caution in selecting their payroll service providers (“PSPs”) following ongoing concerns that some disreputable PSPs may fail to deposit employment taxes, leaving businesses vulnerable to unpaid payroll taxes as well as penalties. Many employers outsource their payroll and related tax duties to third party ...

IRS Releases Additional FAQs on Deferral of Employment Tax Deposits Under Section 2302 of the CARES Act

On July 30, 2020, the IRS released guidance in the form of new frequently asked questions (“FAQs”) addressing the deferral of the employer portion of Social Security taxes under section 2302 of the Coronavirus Aid, Relief, and Economic Security (“CARES”) Act. These FAQs are broad in nature, providing guidance on various considerations relevant to section...… ...

Mnuchin Confirms Trump Payroll Tax Deferral is not Mandatory

Secretary Mnuchin acknowledged in an interview today that the employee Social Security tax deferral envisioned in President Trump’s Presidential Memorandum will not be mandatory. The memorandum instructs the Treasury Department to issue guidance under Section 7508A permitting employers to suspend the withholding, depositing, and payment of the employee’s share ...

Trump Executive Action to Defer Employee Share of Social Security Taxes Raises Significant Legal Questions for Employers

On Saturday, August 8, President Trump signed a Presidential Memorandum directing the Secretary of the Treasury to “use his authority pursuant to [Code section] 7508A to defer the withholding, deposit, and payment of the tax imposed by [Code section] 3101(a) . . . on wages . . . paid during the period of September 1, 2020, through December 31, 2020,” subject...… ...

Senate Bill Would Ignore COVID-19 Assistance in Determining Worker Classification; Treat Certain Benefits as Qualified Disaster Relief Payments

Is an individual service provider an employee or an independent contractor? As our employee benefits colleagues have noted previously in Covington’s Inside Compensation blog, the IRS test is complicated and just one of many for determining worker status under federal and state laws. The American Workers, Families, and Employers Assistance Act (the “Bill”), one ...

Senate Republican Proposal Includes Payroll Tax Credit to Defray Employer Expenses for COVID-19 Prevention

On July 27, Senate Republicans released a series of COVID-19 relief bills, including the “American Workers, Families, and Employers Assistance Act” (the “Bill”). The Bill is a successor to several provisions in the Coronavirus Aid, Relief, and Economic Security (“CARES”) Act, passed in March of this year, which attempted to blunt the early effects of the...… ...

Senate Republican Proposal Would Enhance Employee Retention Credit

As we noted in an earlier post, on July 27, Senate Republicans introduced new legislation in response to the continued COVID-19 pandemic. One of the introduced bills, titled the American Workers, Families, and Employers Assistance Act (the “Bill”), would enhance the existing employee retention credit. The Existing Credit The employee retention credit is a ...

Senate Republican Proposal Would Expand WOTC to Spur Hiring

On July 27, Senate Republicans introduced a series of bills intended as their opening salvo in what appears likely to be contentious negotiations among Senate Republicans, the White House, and House and Senate Democrats over the next legislative response to the COVID-19 pandemic. Along with another round of direct stimulus payments to individual taxpayers, ...

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 Issues Notice 2020-65 Providing Guidance on Employee Social Security Tax Deferral

IRS Warns Employers Claiming New Tax Credits of Erroneous Penalty Notices

IRS Warns Employers to Choose Carefully When Selecting a Payroll Service Provider

IRS Releases Additional FAQs on Deferral of Employment Tax Deposits Under Section 2302 of the CARES Act

Mnuchin Confirms Trump Payroll Tax Deferral is not Mandatory

Trump Executive Action to Defer Employee Share of Social Security Taxes Raises Significant Legal Questions for Employers

Senate Bill Would Ignore COVID-19 Assistance in Determining Worker Classification; Treat Certain Benefits as Qualified Disaster Relief Payments

Senate Republican Proposal Includes Payroll Tax Credit to Defray Employer Expenses for COVID-19 Prevention

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

Senate Republican Proposal Would Enhance Employee Retention Credit

Senate Republican Proposal Would Expand WOTC to Spur Hiring

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