Caroline A. Kupiec
Tax Law
Tax Law
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Caroline has an extensive tax controversy and litigation practice representing taxpayers in front of federal and state taxing authorities at all levels of the audit, controversy and litigation process. Caroline has significant experience representing both individual and business clients before the Massachusetts Appellate Tax Board, and in helping life science and technology clients navigate Massachusetts’ state and local tax landscape. Caroline also has in-depth federal tax controversy and litigation experience, having clerked in the chambers of the Honorable Joesph H. Gale of the United States Tax Court prior to her time at Sullivan, and having represented many individual and business clients before the Internal Revenue Service and in front of the United States Tax Court since.Caroline is a member of Sullivan’s Women’s Initiative and co-chair of the Boston Bar Association’s State and Local Tax Committee. She speaks frequently on Massachusetts tax issues at professional conferences. Caroline has an extensive tax controversy and litigation practice representing taxpayers in front of federal and state taxing authorities at all levels of the audit, controversy and litigation process. Caroline has significant experience representing both individual and business clients before the Massachusetts Appellate Tax Board, and in helping life science and technology clients navigate Massachusetts’ state and local tax landscape. Caroline also has in-depth federal tax controversy and litigation experience, having clerked in the chambers of the Honorable Joesph H. Gale of the United States Tax Court prior to her time at Sullivan, and having represented many individual and business clients before the Internal Revenue Service and in front of the United States Tax Court since.Caroline is a member of Sullivan’s Women’s Initiative and co-chair of the Boston Bar Association’s State and Local Tax Committee. She speaks frequently on Massachusetts tax issues at professional conferences. Caroline has an extensive tax controversy and litigation practice representing taxpayers in front of federal and state taxing authorities at all levels of the audit, controversy and litigation process. Caroline has significant experience representing both individual and business clients before the Massachusetts Appellate Tax Board, and in helping life science and technology clients navigate Massachusetts’ state and local tax landscape. Caroline also has in-depth federal tax controversy and litigation experience, having clerked in the chambers of the Honorable Joesph H. Gale of the United States Tax Court prior to her time at Sullivan, and having represented many individual and business clients before the Internal Revenue Service and in front of the United States Tax Court since. Caroline is a member of Sullivan’s Women’s Initiative and co-chair of the Boston Bar Association’s State and Local Tax Committee. She speaks frequently on Massachusetts tax issues at professional conferences.
Recognized in Best Lawyers since 2026
Ashley King
I engaged Caroline Kupiec at Sullivan & Worcester for a complex Massachusetts DOR audit concerning business expense deductions. Her technical knowledge is evident; she clearly understands the intricacies of tax controversy from the audit level upwards, which gave me initial confidence. Her background and the recognition she's received in tax law are well-deserved from a purely substantive standpoint. She successfully navigated the key issues with the state authorities, and the final resolution was favorable. However, the experience was mixed on the service side. There were periods where responses to emails took a week or more, which was stressful during an active audit. While her analysis was thorough when provided, I sometimes felt I had to prompt for updates rather than receiving proactive communications. The billing was as expected for a firm of this caliber in Boston. In summary, Caroline is a competent and sharp attorney who achieved the legal result I needed. For clients who prioritize constant communication and hand-holding, you may need to set very clear expectations. For those who value deep expertise above all and can manage a less responsive style, her skills in tax litigation are solid.