1) Intention Governs (“Golden Rule”)

The starting point is to give effect to the testator’s actual intentions as revealed by the will. Courts presume a testator did not intend to die intestate; between two plausible readings, they prefer the one that effectively distributes the estate.

2) The “Arm-Chair” Rule

To identify intention, the court “sits in the testator’s chair,” considering the will’s language and the surrounding circumstances known to the testator at signing (family, assets, relationships). This approach traces to Re Burke and remains the modern Ontario starting point. 

3) Interpretation vs. Construction vs. Rectification

• Interpretation: reads the words used, in context, to discern subjective intention.

• Construction: where intention cannot be ascertained, the court imposes a legal meaning to resolve the disposition.

• Rectification (limited): in narrow cases, the court may correct drafting mistakes so the document reflects the testator’s instructions; it is not a licence to rewrite an unambiguous will based on after-the-fact beliefs. See Rondel v. Robinson Estate (2011 ONCA 493) on the limits of rectification and extrinsic evidence.

4) Practical Checklist from Ontario Courts

In Re Kaptyn Estate (2010 ONSC 4293), the court distilled key points often applied in will-interpretation cases, including: focus on actual (not presumed) intention; view the will as a whole; prefer interpretations that lead to testacy over intestacy; use the arm-chair rule (with admissible extrinsic evidence) where appropriate; and in clear cases, correct obvious mistakes to avoid absurd results.

Consider an application where:

• A clause is reasonably capable of more than one meaning and affects distributions.

• There’s tension between the primary and secondary wills, or between will and trust.

• Beneficiaries disagree about what a clause means (e.g., conditions, residue, specific gifts).

• You need clarity before exercising a discretion that could expose you to challenge.

Trustees commonly proceed under Trustee Act, s. 60; in some cases they also seek a “blessing” of proposed steps (sometimes called Cooper orders) so they can administer safely. 

• The document itself (read as a whole).

• Surrounding circumstances known to the testator when the will was made (the arm-chair rule).

• Extrinsic Evidence: admissible to explain context or resolve ambiguity, but not to contradict clear wording or to prove a different, unexpressed intention—limits emphasized by Rondel v. Robinson Estate.