Can your insurance cover a person who has your permission to drive but is not in insurance and has a accidents?

The best advice I can give you as an insurance agent is not to allow people who are not listed on your insurance policy to drive your vehicles, ever. This is not to say your company will not cover someone driving your vehicle with your permission but it will bring up questions. Insurance companies are very wary these days about unlisted drivers who have claims driving an insured vehicle. Your policy states that you must notify all residents of your household as well as any regular driver of any of your vehicles. I have seen several occasions where claims are denied because the insured did not comply with these requirements. This is not to say you can't lend a vehicle to a friend whose car will not start one morning. Just remember you are also loaning them your insurance and your insurance record. How many days makes them a regular driver? A child who lives at college is still a resident of your household. Be very careful jeopardizing your insurance record that you have worked to build up.