memberships & affiliations

  • Fellow and Regent, American College of Tax Counsel
  • Fellow, Maryland Bar Foundation
  • Fellow, Litigation Counsel of America
  • Trustee, Baltimore Bar Foundation
  • MD State Bar Association: Taxation Section - Council (2001 - present); Chair (2008 - 09); Chair-Elect (2007 - 08); Secretary/ Treasurer (2006 - 07); Tax Controversy Group, Founder, Chair (2004-2008), and Advisor (2009 - present)
  • American Bar Association, Section of Taxation - Civil and Criminal Tax Penalties Committee [Vice-Chair (2009-present); Sub-Committee Chair - Important Criminal Developments (2004 - 2008)]; Nominating Committee (2011-2014); Public Fellowship Committee (2009 - 2013); Pro Bono Award Committee (2012 - 2015)
  • Member, Paca Brent Joint Inns of Court
  • Member, Serjeant’s Inn; Member, Rule Day Club
  • Panel Attorney, Criminal Justice Act, U.S. Court of Appeals for the Fourth Circuit
  • Member, Network 2000: Co-chair, Women of Excellence Luncheon (2013, 2014); Member, Board of Directors (2014)
  • Member, Board of Directors, Maryland Volunteer Lawyer Service (2009-present): Chair, Annual Benefits (2012-present)
  • Member, Day 4 Committee (State and Local Tax), Advanced Tax Institute, Maryland State Bar Association and Maryland Association of CPAs (2006 - Present)
  • Member, Advisory Board, Thomson West Tax (2007 – present)
  • Member, Tax Advisory Board, Wolters Kluwer (2013 – present)
  • Member, Advisory Board, Choice Jobs Program (2010 - present)
  • Member, Advisory Board, CCH Journal of Tax Practice & Procedure (2011 – present)
  • Instructor, Military Volunteer Income Tax Assistance (VITA) Program, Fort George G. Meade, Fort Meade, Maryland
  • Sponsor, U.S. Naval Academy Sponsor Program (2013 - present)

awards & honors

  • Chambers USA (2011-2014) Nationwide: Tax Fraud (Band 3)
  • Benchmark: America's Leading Litigation Firms and Attorneys (Future Star, 2012-2014)
  • Best Lawyers in America - Litigation & Controversy – Tax (2011-2015); Lawyer of the Year, Litigation & Controversy - Tax (2012)
  • Nominee (shortlist), Euromoney Legal Media Group's Americas Women in Business Law Awards (Best in Tax Dispute Resolution) (2014)
  • Baltimore SmartCEO Magazine's Legal Elite (2009 & 2010)
  • Maryland Super Lawyers (Tax) (2009-2015); Top 10 Attorneys in Maryland (2013-2015); Top 25 Women Attorneys in Maryland (2009-11); Top 50 Women Attorneys in Maryland (2012-2015); Top 100 Attorneys in Maryland (2010-2015)
  • Featured in CNN Money Magazine – Money Hero (April 2013)
  • Featured on the cover of Maryland Super Lawyers Magazine (2013)
  • Martindale-Hubbell® Bar Register of Preeminent Women Lawyers™
  • Janet R. Spragens Pro Bono Award, ABA Section of Taxation (2010)
  • 2010 Tax Person of the Year (Top 10), Tax Notes/Tax Analysts
  • The Daily Record's Top 100 Women in Maryland (2010, 2012, 2014)
  • The Daily Record's Circle of Excellence (Women in Maryland) (2014)
  • Maryland Volunteer Lawyers Service Educator Award (2008)
  • Judge, Public Service Fellowship, ABA Section of Taxation (2011-2013)
  • Judge, Law Student Tax Challenge, ABA Section of Taxation (2011-present)
  • Judge, Janet R. Spragens Pro Bono Award, ABA Section of Taxation (2012-present)


Caroline D. Ciraolo

On the Cover

Caroline D. Ciraolo was featured on the front cover of Super Lawyers - Maryland 2013 magazine. The cover story, “Chasing the Issue” is featured on page 16.
Read the Full Article

Ciraolo, Caroline

Caroline D. Ciraolo



Practice Groups

About Caroline

To print Caroline's full bio, please click here.

Caroline D. Ciraolo defends individuals and businesses in federal and state civil tax controversies, civil tax litigation, and criminal tax investigations and prosecutions. She is a Fellow and Regent of the American College of Tax Counsel, a vice-chair of the ABA Section of Taxation’s Civil and Criminal Tax Penalties Committee (“CCTP”), and former chair of the Maryland State Bar Association Taxation Section (2008-2009). She has been recognized by Chamber USA (Nationwide: Tax Fraud), Benchmark: American’s Leading Litigation Firms and Attorneys; Best Lawyers in America (Lawyer of the Year (2012), Litigation and Controversy – Tax (Baltimore)), and Maryland SuperLawyers (Top 10 Attorneys, Top 50 Women Attorneys).

Caroline regularly appears on behalf of her clients before the Internal Revenue Service, the Comptroller of Maryland, and the D.C. Office of Tax and Revenue. She litigates cases before the Maryland Tax Court, U.S. Tax Court, and the U.S. District Court, and handles appeals before the Maryland appellate courts and the U.S. Court of Appeals for the Fourth Circuit. Click here for Caroline’s Recent Cases and Speaking Engagements.


  • University of Baltimore School of Law, LL.M. in Taxation (1994)
  • University of Maryland, School of Law, J.D. (Honors) (1993)
  • The College of New Jersey, B.S. in Finance (Honors) (cum laude) (1990)
  • bar admissions

  • Maryland
  • Pennsylvania
  • New Jersey
  • District of Columbia
  • US Tax Court
  • US District Court, District of Maryland
  • US Court of Federal Claims
  • US Court of Appeals, Fourth Circuit
  • US Supreme Court