Holly V.A. Cunliffe TEP


Admitted to the Ontario Bar: 2014

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  • Bio
  • Awards & Recognition
  • Professional Involvement
  • Selected Speaking Engagements
  • Education

Holly focuses on providing her clients with practical solutions to a wide range of estate, trust and capacity issues, helping her clients navigate through emotionally challenging litigation with compassion.

As a member of the firm’s Tax Group and Estates & Trusts Group, Holly represents individuals and trust companies with a range of court proceedings, such as will challenges, applications to pass attorney and trustee accounts, dependent support claims, rectification and interpretation of wills and trusts, variations of trust deeds, power of attorney and capacity disputes, estate and trust administration issues, trustee applications for advice and directions, appointment or removal of trustees/guardians, breaches of trust and guardianships. She is preferred counsel for LawPRO on matters of professional negligence with respect to estate and trust issues.

Holly sits on the executive committees of the Ontario Bar Association’s Elder Law section, and on the executive committee of the Trusts & Estates section. Holly is an accredited Trust and Estate Practitioner (TEP) and active member of the Society of Trust and Estate Practitioners (STEP).

Holly routinely appears before the Ontario Superior Court of Justice (including the Estates and Commercial Lists), and has also appeared before the Court of Appeal for Ontario.

Holly has additional experience in real estate disputes, contract disputes, oppression actions, civil fraud, asset and debt recovery, civil enforcement, employment disputes, product liability, judicial reviews and Indigenous law.

Holly is a longstanding volunteer with Pro Bono Ontario, providing free legal advice to low-income parties appearing in Small Claims Court, and taking calls on the Pro Bono Ontario Free Legal Advice Hotline providing advice on estates, powers of attorney, civil litigation and civil appeals.

Awards & Recognition

  • Recognized as an Associate to Watch in Chambers HNW: The World's Leading High Net Worth Advisers for her expertise in Private Wealth Disputes (Canada)
  • Recognized in The Best Lawyers: Ones to Watch in Canada for her expertise in Trusts and Estates

Professional Involvement


  • The Society of Trust and Estate Practitioners
  • Canadian Bar Association
  • Ontario Bar Association
  • The Advocates' Society

Selected Speaking Engagements

"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. 


  • TEP, Society of Trust and Estate Practitioners, 2021
  • 39th Annual Osgoode Hall Intensive Trial Advocacy Workshop, 2018
  • JD, University of Western Ontario, 2013
  • BA, McGill University, 2007