What Are the Chances of Contesting a Will and Winning?

If you’re considering a will contest, one of the first questions you'll ask is: Do I have a real chance of success? The answer depends on several factors—legal, factual, and procedural. While a will contest can succeed under the right circumstances, it requires solid evidence, clear legal grounds, and timely action. Understanding what courts look for in a will contest will help you assess your position realistically.

1. Legal Grounds Matter More Than Emotion

The most important factor in winning a will contest is whether you have a legally recognized reason to challenge the will. Courts generally accept challenges based on:

• Lack of testamentary capacity
• Undue influence
• Improper execution
• Fraud or forgery
• Failure to provide for a legal dependant

If your objection is based solely on a sense of unfairness or family conflict, your chances are much lower.

2. Strong Evidence is Crucial

You need more than suspicion. Courts rely on documents, credible witness testimony, expert reports (such as from medical or handwriting professionals), and patterns of behavior to support claims. Weak or speculative evidence will not be enough to succeed.

3. Timing Affects Outcome

In Ontario, deadlines matter. For example:

• Dependent support claims: within 6 months after probate is granted
• General claims (e.g., undue influence or lack of capacity): typically within 2 years from the date the claimant knew or ought to have known of the issue

Missing the deadline—even by a day—can eliminate your chance entirely.

4. Who You’re Contesting Against

The strength and credibility of the executor or other beneficiaries can also impact the likelihood of success. If you're contesting a will managed by a professional trustee with detailed records, the burden on you to prove your claim will be higher.

5. Mediation vs. Trial

Many will contests settle through mediation. A strong case may encourage early settlement. A weak one may be dismissed or settled for a nominal amount. Either way, your legal team must be ready to negotiate or litigate depending on the strength of your position.

Key Takeaway

Your chances of success in a will contest depend on the validity of your claim, the quality of your evidence, and your timing. Consulting an estate litigation lawyer early is essential to building a strong case and protecting your rights.

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