Holly Cunliffe

Holly focuses her practice on estate, trust and mental capacity litigation. She is known for delivering practical, results-driven solutions in matters that are often highly personal and emotionally challenging.

Holly is a member of the firm’s Tax and Trusts & Estates Groups, and Co-Leader of the Estate Litigation Group. She has extensive experience representing executors, trustees, beneficiaries, attorneys, guardians and concerned family members. Holly provides legal counsel on a wide variety of matters related to inheritance, power of attorney and guardianship. Additionally, she represents clients in complex litigation where an estate or trust is involved, including oppression proceedings in closely held family businesses. Holly frequently advises on legal issues such as will challenges, gift disputes, will and trust interpretation issues, passing of accounts, dependent support proceedings, mental capacity disputes, guardianship appointments, executor or trustee removals, complex estate and trust administration disputes, defending both trustee and executor conduct, will and trust variations and applications for advice and direction of the court.

Holly is a recognized leader in her field. She is a licensed Trust and Estate Practitioner (TEP) with the Society of Trust and Estate Practitioners (STEP). Holly is currently one of only 12 elected STEP worldwide members who form the steering committee for the global Mental Capacity Special Interest Group, staying at the forefront of mental capacity issues that affect succession planning and inheritance matters. Holly was an Executive Committee Member of the Ontario Bar Association’s Elder Law Section from 2019-2025 and an Executive Committee Member of the Trusts & Estates Section from 2021-2022.

Holly routinely appears before the Ontario Superior Court of Justice and the Court of Appeal for Ontario.

Selected Speaking Engagements

"Understanding Capacity and Managing Our Own Emotions," STEP Atlantic Seminar, March 26, 2026.

"Definition of a Dependant," Essential Skills for Estate Litigators: Litigating Threshold Issues, May 13, 2025.

"Recognising and Tackling Vulnerable Client Abuse," STEP Global Congress, Rome, Italy, February 25-26, 2025.

"Pitfalls in Capacity Litigation and Facilitating Solutions," OBA Elder Law Program, December 6, 2023.

"Orders For Directions” in Dependant Support Proceedings, Will Challenges, and Attorney/Guardianship Disputes, OBA Trust & Estate Law, May 16, 2023.

"Decision Making by the Declining Mind: How Friends and Family Can Help, and the Risk for Abuse," Aird & Berlis LLP Estates & Trusts Webinar, March 21, 2022.

"Overview of Common Will Challenges,” OBA's “Estate Litigation: A Primer” Webinar, February 22, 2022.

"Claims for Dependant Support," Junior Trust and Estate Practitioners (JTEP), July 19, 2021.

"Your First Estate Administration – Family Law Issues," OBA Trusts and Estates Law / Young Lawyers Division, June 17, 2021.

Mental Capacity Global SIG Steering Committee, The Society of Trust and Estate Practitioners, 2020-present

Elder Law Section Executive, Ontario Bar Association, 2019-2025

Executive Committee Member, Trusts & Estates Section, Ontario Bar Association, 2021-2022

Canadian Bar Association

Ontario Bar Association

The Advocates' Society