When to File a Demand Letter — And When Not To

August 19, 2025

A practical guide to using demand letters for debt, contracts, and disputes.

Ontario paralegal preparing and sealing a demand letter envelope with scales of justice and laptop on desk

If you’re owed money, facing a contract dispute, or dealing with someone who isn’t holding up their end of an agreement, you may have heard about using a demand letter. But is it always the right move? As Ontario paralegals, we often see clients who could benefit from a demand letter — and others where it may not be the right first step. This guide will help you understand when to use a demand letter, and when not to, so you can make a smart legal decision.


What Is a Demand Letter?

A demand letter is a formal written notice sent to another party, asking them to take (or stop) a specific action. Most often, it’s used to:

  • Request payment of an outstanding debt.
  • Enforce a contract or agreement.
  • Resolve disputes before going to court.
  • Provide evidence of your attempts to settle matters reasonably.


In Ontario, a properly drafted demand letter can save you time, money, and stress — and it often leads to a resolution without needing a lawsuit.


When You Should File a Demand Letter

1. When You’re Owed Money

If someone hasn’t paid an invoice, loan, or service fee, a demand letter shows you’re serious. It can often prompt payment without further legal steps.


2. When Contracts Are Broken

Whether it’s a landlord/tenant agreement, service contract, or business deal, a demand letter can formally outline how the other party has failed to meet their obligations.


3. When You Want to Avoid Court

Courts often expect you to try reasonable steps before filing a claim. A demand letter proves you attempted resolution, which strengthens your case if it moves forward.


When You Shouldn’t File a Demand Letter

1. When Emotions Are High

If the dispute is deeply personal (like a family matter), sending a legal letter too soon may escalate tensions instead of solving the issue.


2. When There’s No Legal Basis

If the claim is weak or unsupported, sending a demand letter could backfire. The other side may call your bluff — or worse, use it against you later in court.


3. When Time Is Critical

If a limitation period is about to expire, filing a claim right away might be safer. A demand letter alone won’t stop the clock on deadlines.


How a Paralegal Can Help

A well-drafted demand letter is professional, persuasive, and legally grounded. At Cordaie Paralegal Services, we:

  • Review your case and determine if a demand letter is appropriate.
  • Draft clear, legally sound letters that carry authority.
  • Advise you on next steps if the letter doesn’t resolve the matter.


Key Takeaway

A demand letter can be a powerful tool — but it isn’t right for every situation. Filing one at the wrong time, or without legal advice, can hurt your chances of success.


If you’re unsure whether a demand letter is the right move for your situation, speak with a licensed Ontario paralegal. The right guidance can save you from unnecessary stress and set you on the path to resolution.


Call to Action

Ready to take the next step? Contact Cordaie Paralegal Services today for a consultation. We’ll help you decide whether a demand letter is the right strategy — and handle the process from start to finish.


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