Does an employee's benefits waiting period restart under a new owner, or does it carry over?

This depends on two separate things: statutory continuity of service, and the actual terms of whatever benefits plan you put in place, which aren't necessarily the same question. Under the Employment Standards Act, if an employee is hired as part of a going-concern business sale, their service is treated as continuous for statutory entitlement purposes, but that doesn't automatically dictate the terms of a specific group benefits plan, which is a separate insurance product with its own eligibility rules.

If you're continuing the seller's existing benefits plan without change, a waiting period an employee already satisfied generally shouldn't need to restart, since nothing about their coverage eligibility has actually changed. If you're moving employees onto a new benefits plan with your own insurer, that plan's own terms govern eligibility, and many insurers will waive or credit a new waiting period for employees transferring from an existing group plan without a break in coverage, but this depends entirely on your specific policy and insurer, not on the Employment Standards Act.

Confirm your new benefits carrier's specific transfer and waiting-period rules directly, rather than assuming statutory continuity automatically extends to insurance eligibility. A Treadstone business lawyer can help coordinate this with your broader employee transition.