Karen L. McKenna

Karen L. McKenna is a partner in the Trusts, Estates and Fiduciary Management group in Shipman’s Boston office.  She counsels individuals, families, and fiduciaries on all aspects of estate planning, trust and estate administration, and related tax matters. With more than two decades of experience, she works with clients to structure plans that protect wealth, minimize tax exposure, and ensure smooth transitions across generations.

Karen’s work spans the design of estate, gift, and generation-skipping transfer tax strategies for high-net-worth individuals to guiding personal representatives and trustees through the practical and legal responsibilities of estate administration. She is frequently called upon to advise in matters involving probate proceedings, fiduciary disputes, and contested estates, where her ability to balance technical knowledge with sensitivity to family dynamics is especially valuable.

Her practice often bridges planning and litigation. Karen collaborates closely with the firm’s litigation team on matters such as will contests, breach of fiduciary duty claims, and complex accountings. This dual perspective allows her clients to anticipate potential areas of conflict during the planning phase and to rely on her advocacy should disputes arise.

Clients appreciate Karen’s ability to make complex tax rules understandable and to deliver clear, actionable plans tailored to their needs. She has handled cross-jurisdictional planning involving Massachusetts and Pennsylvania, giving her additional perspective on how differing state laws affect multi-state families and estates. Her early career in accounting enhances her approach to tax compliance and planning, ensuring that legal strategies are informed by a sound financial foundation.

Beyond her practice, Karen contributes her time and leadership to the community, including service on nonprofit boards and volunteer work in animal welfare. Clients know her as a careful listener, a practical problem-solver, and a trusted advisor who combines technical ability with a commitment to client service.