Uninsured handyman/painter with Umbrella insurance

Jurisdiction
New York
Guys - I'd like to confirm that Umbrella insurance typically won't cover anything that the primary home insurance wouldn't cover right? For e.g. if a painter who's not bonded and doesn't have worker's insurance (just someone who does side jobs) and falls off my roof, my umbrella insurance is unlikely to cover him and I'll have a lawsuit waiting for me correct?

Thanks
 
Whenever you hire someone to do work on your property you ask for a certificate of insurance to prove that they are insured for liability. If they can't or will not show you the certificate you say thank you but no thanks. Better yet, you ask for a certificate naming you as additionally insured.

Some states like NY will exempt a sole proprietor (without employees) from the workman's comp insurance requirement but they must carry liability insurance.
 
For e.g. if a painter who's not bonded and doesn't have worker's insurance (just someone who does side jobs) and falls off my roof, my umbrella insurance is unlikely to cover him and I'll have a lawsuit waiting for me correct?

The first thing this question makes me wonder is why a painter is on your roof. In any event, if you hire a painter and he falls off your roof, your potential liability would depend on the reason(s) why the painter fell. If he fell for reasons other than your negligence, you should have no legal liability. Of course, that doesn't mean you wouldn't get sued, but that's one of the reasons why you have homeowner's insurance. Also note that the lack of a bond or "worker's insurance" (by which I assume you mean workers' compensation insurance) would have no relevance whatsoever. In such a situation, if you have an umbrella policy, it should cover liability in excess of your homeowner's policy (and, if it doesn't, you should consult with an agent about obtaining better coverage).
 
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