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- S. Michael Chittenden
S. Michael Chittenden

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.
- 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.
Memberships and Affiliations
- American Bar Association, Section of Taxation
- The District of Columbia Bar, Taxation Section
February 8, 2021, Tax Withholding & Reporting Blog
Recently released IRS Notice 2021-11, implements the extension of the period for collecting from employees and depositing employee Social Security tax that was deferred in the last four months of 2020. IRS Notice 2020-65 (see earlier coverage) had specified that the employer “must withhold and pay the total [deferred 2020 taxes] . . . ratably...… Continue ...
February 2, 2021, Tax Withholding & Reporting Blog
In Announcement 2021-2, released on February 1, the IRS instructed lenders not to report loan relief payments made by the Small Business Administration under Section 1112(c) of the Coronavirus Aid, Relief, and Economic Security (“CARES”) Act. The Announcement reflects a provision in the Consolidated Appropriations Act, 2021 (the “CAA”), excluding such payments ...
January 29, 2021, Tax Withholding & Reporting Blog
As described in our previous post, on December 21, 2020, another round of COVID relief legislation was passed, providing an enhanced employee retention credit (“ERC”) with various new features and greater benefit amounts. The legislation was subsequently enacted when President Trump signed the law on December 27. On January 26, the IRS issued a news...… ...
January 8, 2021, Tax Withholding & Reporting Blog
On January 4, 2021, the Internal Revenue Service issued Notice 2021-7 pertaining to the valuation of the personal use of employer-provided vehicles. The Notice permits employers who rely on the special valuation rule of Treasury Regulation § 1.61-21(d), known as the Automobile Lease Valuation (ALV) method, to retroactively apply the vehicle cents-per-mile ...
December 24, 2020, Tax Withholding & Reporting Blog
As the end of the year approaches, many accounts payable departments are gearing up to complete their annual Form 1099 filings. For 2020, a new form, Form 1099-NEC, will be used to report payments of non-employee compensation to vendors. (See earlier coverage.) The IRS resurrected the Form 1099-NEC, which had not been used in decades,...… Continue Reading
December 22, 2020, Tax Withholding & Reporting Blog
After months of gridlock, the House and Senate, on December 21, both passed another round of COVID relief legislation (H.R. 133). The 5,593-page bill, which gained momentum following the introduction of bipartisan compromise legislation, provides an enhanced employee retention credit (“ERC”), which is easier for employers to qualify during the first six months ...
December 21, 2020, Tax Withholding & Reporting Blog
On Friday, December 18, the IRS released final regulations under section 162(m) implementing the statutory changes made in 2017 by the Tax Cuts and Jobs Act. Section 162(m), as amended, generally limits the deduction for compensation (also referred to as applicable employee remuneration) paid to the a publicly held corporation’s principal executive officer ...
December 15, 2020, Tax Withholding & Reporting Blog
For employers who decided to defer the employee share of Social Security taxes on wages paid from September 1 to December 31, 2020, pursuant to President Trump’s August 8 presidential memorandum, the employer’s obligation to collect those deferred amounts from employees’ paychecks is fast approaching. Included among our previous posts discussing the deferral, ...
What You Can Do to Protect Your Dependent Care FSA Cash
December 11, 2020, The Wall Street Journal
Michael Chittenden is quoted in The Wall Street Journal regarding the options for excess FSA dependent-care spending. Mr. Chittenden says the best option is to find expenses to claim. There are strict limits on what expenses the IRS considers eligible, and employers and plan administrators don't have flexibility to alter the rules. Most importantly, expenses ...
December 10, 2020, Tax Withholding & Reporting Blog
Yesterday, December 9, the IRS released final regulations implementing the Section 274(a)(4) and 274(l) deduction disallowances, adopted as part of the 2017 Tax Cuts and Jobs Act. Section 274(a)(4) disallows employer deductions for the cost of providing qualified transportation fringe (“QTF”) benefits provided to employees. Section 274(l) provides a broader ...
December 2020, LexisNexis Practical Guidance
IRS FAQs Provide Welcome Guidance on Employee Retention Credit and PPP Loans in M&A Transactions
November 18, 2020, Tax Withholding & Reporting Blog
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
July/August 2020, Corporate Taxation
March 26, 2020, Covington Alert
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 ...
July 10, 2018, Covington Alert
For only the third time in the last fifty years, the Supreme Court has ruled on whether a state may compel a remote, out-of-state seller to collect and remit that state’s sales tax on purchases made by in-state customers.
- Washington, DC Super Lawyers, “Rising Star” Tax and Employee Benefits (2015-2017)

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