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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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

Tax Court Reverses Course on TFRP after Remand from Eleventh Circuit

By S. Michael Chittenden and Michael M. Lloyd on Posted in Court Cases, Employment Taxes, IRS
On remand from the Eleventh Circuit, the Tax Court, in Romano-Murphy v. Comm’r, determined that the failure of the IRS to provide a pre-assessment appeals hearing invalidated the IRS’s assessment of trust fund recovery penalty under section 6672 and proposed levy to collect the same.  In July 2006, the IRS sent a letter to the … Continue Reading

TIGTA Chides IRS for Lax Non-Payroll Withholding Enforcement

By S. Michael Chittenden and Michael M. Lloyd on Posted in Information Reporting, IRS
The Treasury Inspector General for Tax Administration released a partially redacted report on May 20 asserting that the IRS has failed to take steps to address nearly $2 billion in discrepancies between withholding reported on withholding tax returns and withholding reported on information returns.  The TIGTA report found that 7,265 taxpayers reported nearly $925 million … Continue Reading

Justice Department Announces Employment Tax Enforcement Actions

By Michael M. Lloyd and S. Michael Chittenden on Posted in Court Cases, Employment Taxes
Consistent with its ongoing employment tax enforcement efforts, the Justice Department recently announced developments in two cases involving the failure to properly withhold and remit federal employment taxes from employee wages. On April 25, the Justice Department announced that Kae Wook Lee, the sole owner and CEO of Mona Lisa 7 Corporation, was sentenced to … Continue Reading

IRS Again Addresses De Minimis Standard for Third Party Network Transactions

By Pooja Shah Kothari, Michael M. Lloyd and S. Michael Chittenden on Posted in Information Reporting, IRS
For the second time in the past year, the IRS Office of Chief Counsel issued a ruling addressing how transactions are counted for purposes of applying the de minimis threshold applicable to third party settlement organizations (“TPSOs”) under section 6050W.  In recently released PLR 201907006, the IRS considered the facts related to a payment processing … Continue Reading

IRS Targets Backup Withholding Compliance

By Michael M. Lloyd and S. Michael Chittenden on Posted in Information Reporting, IRS
Dan Lauer, an IRS executive for SBSE, told an audience at the American Payroll Association’s Capital Summit on March 25 that the Service is launching a program in the summer of 2019 to pursue backup withholding failures.  Backup withholding is required under section 3406, and the current backup withholding rate is 24%.  Generally, backup withholding … Continue Reading

Federal Court Allows Claim to Proceed Against Employer for Fraudulent W-2s

By Michael M. Lloyd and S. Michael Chittenden on Posted in Court Cases, Employment Taxes, Worker Classification
On March 5, 2019, the U.S. District Court for the District of Maryland determined that an employee was potentially entitled to relief under section 7434(a) of the Internal Revenue Code when an employer purposefully reports a portion of their wages on Form 1099-MISC as income from self-employment rather than on the Form W-2.  In Greenwald … Continue Reading

Bill Seeks to Provide Worker Classification Safe Harbor and Update Reporting Thresholds

By Michael M. Lloyd and S. Michael Chittenden on Posted in Legislation, Tax Reform
On March 7, 2019, Senator John Thune (R-SD) reintroduced legislation aimed at simplifying worker classification and requiring additional wage reporting under certain circumstances.  Senator Thune introduced the New Economy Works to Guarantee Independence and Growth Act (the “New GIG Act”) for the first time in 2017.  It was included in the chairman’s mark of the … Continue Reading

IRS Issues Action on Decision in Jacobs v. Commissioner

By Pooja Shah Kothari, Marianna G. Dyson and S. Michael Chittenden on Posted in Court Cases, IRS
On February 19, 2019, the IRS issued AOD 2019-01, 2019 IRB 569, acquiescing in the result only in the Tax Court’s decision in Jacobs v. Commissioner, 148 T.C. 24 (2017). (Earlier coverage, here.)  By virtue of the AOD on Jacobs, the IRS indicated its acceptance of the Tax Court’s holding and will follow Jacobs “only … Continue Reading
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