In Ontario the owner of the vehicle is required to insure it. The owner’s policy (OAP 1) generally lists drivers that are regular operators of the vehicle.
There may be an occasion where you need to lend your vehicle. Provided the operator holds a valid operators licence and has your permission as the owner, they can drive your vehicle, BUT they are driving on your insurance. This means, any losses that occur can and will be rated against you as the owner.
The auto insurance contract does require you disclose regular operators and drivers residing in your household without their own car and insurance. Failure to do so may create a material change in risk after an unlisted driver causes a claim, which could result in the cancellation of your policy.