Will I lose my benefits the day the new owner takes over?

Not automatically, but it depends on exactly how the sale is structured. If the new owner is buying the shares of your employer, your employer hasn't changed, so your existing benefits plan should simply continue unless the company itself later decides to change carriers or coverage.

If the new owner is instead buying the business's assets and hiring you as an employee of their own company, your years of service count toward statutory entitlements like vacation under the Employment Standards Act, 2000 — but that continuity rule doesn't force the new owner to keep the seller's specific benefits plan. A new employer can offer its own plan, which might have different coverage, different waiting periods, or a different insurer entirely.

The real risk is a coverage gap between the seller's plan ending and the new owner's plan starting, so ask before closing exactly when the old coverage ends and the new coverage begins. If there's any gap, some claims — a prescription refill, for instance — may need to wait, so timing your paperwork and any pending claims around the transition is a genuinely useful, practical step to take now.