Tax Relief Tactics: Mastering IRS Penalties, Fines and Interest Abatement

Phillip J. Colasanto | Withers Bergman LLP

Phil is a senior associate at Withers Bergmen LLP (Withers Worldwide). Phil’s practice is focused on domestic and international tax controversy. He has represented clients before the U.S. Tax Court, U.S. district court, U.S. Court of Appeals, and various state courts. He has represented clients from audit through trial and, if necessary, at the appellate level.

Phil has spoken on various tax topics and at various forums, including the American Bar Association, New York County Lawyers’ Association, IRS Nationwide Virtual Tax Forum, CPA Academy, and NYU Tax Controversy Forum. He has also published several tax-related articles, which have been published by Tax Notes, Bloomberg BNA, Journal of Tax Practice and Procedure, EA Journal, and The Practical Lawyer. In addition to his publication and speaking engagement, he is heavily involved with the American Bar Association, where he is the Chair of the Tax Collections Bankruptcy and Workouts Committee.

Phil is a former American Bar Association John S. Nolan Fellow (2019 2020). He also provides pro bono service for taxpayers and was awarded the New York County Lawyers’ Association Pro Bono Award in 2022.

Gray Proctor | Kostelanetz LLP

Gray Proctor, Vanderbilt ’07, practices tax controversy as counsel at Kostelanetz LLP’s Atlanta office. He is board-certified as an expert in civil appellate matters by the Florida Bar Association. He is also admitted to practice in Georgia, as well as the Tax Court and federal Circuit Courts of Appeals for the First, Second, Third, Fourth, Fifth, Sixth, and Eleventh Circuits.

Session I – Correcting Noncompliance and IRS Penalty Relief | 2:00pm – 3:00pm

• Correcting prior noncompliance
  • Taxpayer noncompliance
  • Options for correcting noncompliance
  • Strategies for improving taxpayer compliance
• Understanding IRS penalties
  • IRS penalties
    • Failure to file penalty
    • Failure to pay penalty
    • Accuracy-related penalties
    • Underpayment of estimated taxes
    • Civil fraud penalty
    • International penalties
  • Calculation methods for penalties and interest
• Penalty abatement procedures
• Criteria for first-time abatement
  • Reasonable cause arguments
  • Procedural arguments
  • Documentation and evidence for successful abatement requests

Break | 3:00pm – 3:10pm

Session II – Penalty Defense: Reasonable Cause + A Few More | 3:10pm – 4:10pm

• Reasonable cause: The heartland penalty defense
• Loper Bright and challenges to unfavorable regulatory definitions of “reasonable cause”
• Jarkesy and the constitutional role of juries in tax penalties