If a charity named in my will has shut down, can a court redirect the gift to a similar cause under cy-près?

In some circumstances, yes. When a named charity no longer exists at the time the gift is meant to take effect, Ontario courts can apply the cy-près doctrine to redirect the gift to a similar charitable purpose, rather than letting it fail entirely, but this isn't automatic and depends on the specific facts. Generally, the court needs to be satisfied that you had a "general charitable intention," wanting to support a type of cause, rather than an intention tied so specifically to that one organization that no substitute would reflect your wishes.

Whether cy-près applies, and where the money ultimately goes, is a case-by-case determination, and the process typically involves the estate trustee, sometimes Ontario's charitable oversight bodies, and potentially a court application, none of which is guaranteed to produce the exact outcome you might have wanted.

Because outcomes here aren't certain, the better practice is to avoid relying on cy-près after the fact. Naming an alternate charity, or a broader category of purpose, directly in your will gives clearer instructions and reduces the chance of a dispute or an unwanted result if your first-choice charity no longer exists when the time comes.