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.

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IRS Releases Proposed Regulations on the Mechanics of Income Tax Withholding

By Sarah Friedman, S. Michael Chittenden and Marianna G. Dyson on Posted in Employment Taxes, IRS, Tax Reform
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

By Michael M. Lloyd and S. Michael Chittenden on Posted in Backup withholding, Chapter 3, Employment Taxes, FATCA, IRS, Justice Department, Trust fund taxes
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

By Michael M. Lloyd and S. Michael Chittenden on Posted in Employment Taxes, IRS, Tax Reform
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 adjusting … Continue Reading

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

By Sarah Friedman and S. Michael Chittenden on Posted in Employment Taxes
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 Reading

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

By Xueshu ("Shae") Qian and S. Michael Chittenden on Posted in Chapter 3, IRS
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 … Continue Reading

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

By S. Michael Chittenden, Marianna G. Dyson and Michael M. Lloyd on Posted in Executive Compensation, IRS, Tax Reform
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 … Continue Reading

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

By Molly Ramsden, Michael M. Lloyd and S. Michael Chittenden on Posted in Affordable Care Act, Employee Benefits, Information Reporting, IRS, Legislation, Tax Reform
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 penalty through the Tax Cuts … Continue Reading

The IRS Introduces More Informative Backup Withholding Notices for Payers

By Jeffrey Zink, Michael M. Lloyd and S. Michael Chittenden on Posted in Backup withholding, Information Reporting, IRS
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 Reading

Significant TCJA Guidance Due Before End of Year, Kautter Says

By Joseph Sullivan, Michael M. Lloyd and S. Michael Chittenden on Posted in Employment Taxes, Executive Compensation, IRS, Legislation, Tax Reform
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 executive … Continue Reading

November 15 Deadline Approaching for 2019 Qualified Intermediary Applications

By Michael M. Lloyd, S. Michael Chittenden and Jeffrey Lash on Posted in Chapter 3, FATCA, IRS
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.… Continue Reading

Proposed Regulations Provide Guidance for Classification of Digital Content Transactions and Cloud Transactions

By Michael M. Lloyd, S. Michael Chittenden and Jeffrey Lash on Posted in Chapter 3, Information Reporting, IRS
On August 9, 2019, Treasury and the IRS issued proposed regulations under section 861 of the Code to clarify how transactions involving digital content and cloud computing are classified for tax purposes.  The new rules propose to revise and expand upon Treasury Regulation § 1.861-18 regarding digital content transactions and establish new Treasury Regulation § … Continue Reading

MyPayrollHR Scandal Serves as Reminder to Verify Employment Tax Deposits

By S. Michael Chittenden and Marianna G. Dyson on Posted in Employment Taxes
Although the facts are still unfolding, recent developments surrounding the collapse of payroll firm MyPayrollHR serve as a reminder to employers to regularly verify the actions of payroll service providers.  This should be a routine practice, regardless of the provider’s reputation and the longevity of the relationship.  In particular, employers should open their own EFTPS … Continue Reading

IRS Releases Updated Tax Withholding Estimator

By S. Michael Chittenden and Marianna G. Dyson on Posted in Employment Taxes, IRS, Tax Reform
Today, the IRS unveiled its new Tax Withholding Estimator to help employees complete the Form W-4 and ensure that withholdings are sufficient to cover their income tax liability.  The new calculator was previewed in the draft 2020 Form W-4.  (See earlier coverage.)  A near-final draft 2020 Form W-4 is expected to be released soon.  Currently, … Continue Reading

IRS Rules 23andMe’s Home DNA Kit Eligible for Partial FSA Reimbursement

By S. Michael Chittenden and Marianna G. Dyson on Posted in Employee Benefits, Fringe Benefits, IRS
In May, the IRS issued a private letter ruling to an individual taxpayer regarding the deductibility of 23andMe’s at-home DNA test kits under section 213(d) of the Code, which permits the deduction of medical expenses.  In the ruling, the IRS determined that an allocable portion of the purchase price may be treated as a deductible medical … Continue Reading

New Rule Permits Employers to Include Truncated TINs on Forms W-2 and Forms W-2c

By James Damon and S. Michael Chittenden on Posted in Information Reporting, IRS, Legislation
Yesterday, the IRS released final regulations that aim to prevent identity theft by permitting, but not requiring, employers to truncate the taxpayer identification numbers (TINs) on copies of Forms W-2 and Forms W-2c furnished to employees.  The regulations finalize proposed rules issued in 2017.  Generally, this rule applies to Forms W-2 required to be filed or … Continue Reading

D.C. Starts Collecting Taxes to Fund New Paid-Leave Program

By Molly Ramsden and S. Michael Chittenden on Posted in Employee Benefits, Employment Taxes
In 2017, the District of Columbia passed the Universal Paid Leave Amendment Act of 2016 (the “Act”), which called for the creation of a paid-leave program for private sector employees who work in D.C. Earlier this year, the D.C. Office of Paid Family Leave adopted final regulations to implement this new paid-leave program. One of … Continue Reading

IRS to Launch FATCA Compliance Campaign for FFIs

By S. Michael Chittenden and Michael M. Lloyd on Posted in FATCA, Information Reporting, IRS
Last week, the Acting Director of IRS of Field Operations for the LB&I Foreign Payments Practice (“FPP”) announced that the IRS will launch a compliance campaign this summer focused on foreign financial institutions (“FFIs”) that are not satisfying their reporting obligations under the Foreign Account Tax Compliance Act (“FATCA”).  Speaking at a tax controversy forum … Continue Reading

IRS Warns Withholding Agents to Consider FPP Correction Program to Avoid Penalties

By Pooja Shah Kothari, Michael M. Lloyd and S. Michael Chittenden on Posted in Chapter 3, FATCA, IRS
Last week, Kimberly Schoenbacher, the Acting Director of Field Operations for the LB&I Foreign Payments Practice (“FPP”), sent a message to taxpayers who may be noncompliant with Chapter 3 and FATCA withholding and reporting: the IRS is actively honing in on Form 1042 nonfilers, Form 1042 failures, and Forms 1042 and 1042-S that do not … Continue Reading

Draft 2020 Form W-4 Addresses Some Privacy Concerns

By S. Michael Chittenden, Marianna G. Dyson and Michael M. Lloyd on Posted in Employment Taxes, IRS
On May 31, the IRS released a draft 2020 Form W-4 that addresses some, but not all, of the privacy concerns that led the IRS to abandon the redesigned form for 2019.  According to an accompanying news release, the IRS anticipates releasing a near-final form in July to allow payroll processors and employers to begin … Continue Reading

IRS Legal Memo Addresses Payroll Compliance when Employer Appoints Agent in the Middle of Calendar Year

By Michael M. Lloyd and S. Michael Chittenden on Posted in Employment Taxes, Information Reporting, IRS
On May 31, the IRS released a legal memorandum, ILM 201922026, regarding the information return obligations of a common law employer when it appoints a pay agent in the middle of a calendar year.  In general, an employer may appoint a pay agent under section 3504 by using IRS Form 2678 (Employer/Payer Appointment of Agent) … Continue Reading

Proposed 3405 Withholding Regulations Three Decades in the Making

By S. Michael Chittenden and Michael M. Lloyd on Posted in Employment Taxes, IRS
In 1987, the IRS released Notice 87-7 providing guidance on whether certain recipients of payments from employer deferred compensation plans, individual retirement plans, and commercial annuities are subject to federal income tax withholding under section 3405.  The notice provided that: payors must withhold on periodic and nonperiodic payments under section 3405(a) or 3405(b), respectively, to payees … Continue Reading

Final CPEO Rules Signal Loosened Bond Requirements, Clarify Other Provisions

By Marianna G. Dyson and S. Michael Chittenden on Posted in Employment Taxes, IRS
On May 23, the IRS and Treasury released final regulations governing certified professional employer organizations (“CPEOs”).  CPEOs were created by the Tax Increase Prevention Act of 2014, P.L. 113-295, which added new Code sections 3511 and 7705 that contain certification requirements for, and the federal employment tax consequences of, being a CPEO.  The measure, passed … Continue Reading
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