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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

Senate-Passed COVID-19 Legislation Includes Payroll Tax Provisions

Late Wednesday night, the Senate passed (96-0) the Coronavirus Aid, Relief, and Economic Security (“CARES”) Act, the third Coronavirus-related piece of legislation. Early Wednesday, the Senate announced that an agreement had been reached among Senate Republicans, Senate Democrats, and the Trump Administration on the package, but late concerns from a quartet of ...

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 ...

IRS Offers Informal Guidance on New Paid Leave Tax Credits; More to Come Next Week

Earlier this evening, the IRS offered informal guidance in IR-2020-57 regarding its administration of the payroll tax credits enacted as part of the Families First Coronavirus Response Act (the “Act”) earlier this week. The Act mandates two forms of paid leave for employees of employers of 500 or fewer employees. Employers of more than 500...… Continue Reading

COVID-19 Emergency Declaration: Notice 2020-17 Suggests Code § 139 is Available to Provide Tax-Free Payments for Certain Expenses

In an earlier alert, we expressed concern about the applicability of Section 139. Our concern was based on the fact that the President’s declaration of an emergency on March 13, 2020, with respect to the COVID-19 pandemic was under Section 501(b) of the Robert T. Stafford Disaster Relief and Emergency Assistance Act (the “Stafford Act”)...… Continue Reading

Paid Leave Measure Enacted in Response to COVID-19 Outbreak

UPDATE: President Trump signed the bill into law this evening. This afternoon, the Senate voted 90-8 to approve the House-backed Families First Coronavirus Response Act. The legislation will provide up to ten weeks of paid FMLA leave and two weeks of paid sick leave to certain employees affected by COVID-19. Details on the legislation, which...… Continue ...

House-Passed Coronavirus Relief Bill Leaves Many with More Questions than Answers

This weekend, the House of Representatives passed the Families First Coronavirus Response Act, a relief bill negotiated with the agencies and supported by the President. On Monday night, the House of Representatives substantively modified that bill in a follow-on resolution, H. Res. 904, referred to as technical corrections. Despite the changes, concerns have ...

COVID-19 Emergency Declaration: Code § 139 Uncertain; Leave-Sharing Policies Permitted

UPDATE: We have provided an updated analysis of the issues surrounding the availability of Section 139. Our original post is below. On March 13, 2020, the President declared the COVID-19 pandemic to be an emergency under Section 501(b) of the Robert T. Stafford Disaster Relief and Emergency Assistance Act (the “Stafford Act”). The decision to...… Continue ...

New Treasury Regulations Ease Payroll Administration Related to Employer-Provided Vehicles

For decades, employers and employees have been effectively precluded from using two of the handiest special valuation rules—the fleet-average and vehicle cents-per-mile valuation rules—to value employees’ personal use of employer-provided vehicles. The 1989 fringe benefit regulations imposed modest maximum vehicle values ($16,500 and $12,800, respectively, as ...

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 ...

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S. Michael Chittenden

Representative Matters

Memberships and Affiliations

News and Insights (Showing 5 of 13) (Showing 13 of 13)

Senate-Passed COVID-19 Legislation Includes Payroll Tax Provisions

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

IRS Offers Informal Guidance on New Paid Leave Tax Credits; More to Come Next Week

COVID-19 Emergency Declaration: Notice 2020-17 Suggests Code § 139 is Available to Provide Tax-Free Payments for Certain Expenses

Paid Leave Measure Enacted in Response to COVID-19 Outbreak

House-Passed Coronavirus Relief Bill Leaves Many with More Questions than Answers

COVID-19 Emergency Declaration: Code § 139 Uncertain; Leave-Sharing Policies Permitted

New Treasury Regulations Ease Payroll Administration Related to Employer-Provided Vehicles

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

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