Are you registered with my local building department, and will you pull the permit through them directly?

Every municipality has its own building department, and contractors must be registered to pull permits locally. A contractor who isn't registered in your area either can't pull the permit or will ask you to. Both are red flags.

Will you pull the permit, and is that included in the price?

Unpermitted work can cause serious problems when you sell your home or file an insurance claim. The contractor should handle permits. If they suggest skipping it "to save money," or ask you to pull a homeowner's permit yourself, walk away.

Can you provide a current certificate of insurance showing general liability and workers' compensation coverage?

If a worker is injured on your property or your home is damaged during the job, you want their insurance covering it, not yours. Don't be afraid to ask for proof of insurance before work begins. A reputable contractor should have no problem providing it.

How long have you been operating in this area, and can you provide 3 local references?

Storm-chasing contractors appear after every hail event, do the work, and leave. Local companies have a reputation to protect and will be here when you need warranty service.

Are you a certified installer for the materials you're recommending?

Manufacturer warranties on shingles and windows often require certified installation. If the installer isn't certified, you may void the product warranty before the job is even finished.

Is this a firm written estimate?

Never sign anything without a written estimate in hand. The best contractors provide estimates that are detailed and clear about what is included and what the expectations are. Vague estimates protect the contractor. Transparent ones protect you.

What exactly is included and what is not?

The lowest bid isn't always the lowest price. Vague scopes leave room for unexpected charges mid-project that can push your final cost well above a more transparent competitor's quote. Ask exactly what's included before you sign and get the answer in writing.

How do you handle unforeseen damage discovered mid-project?

Rotted decking, damaged underlayment, failed flashing. This comes up. Ask for their process: will they stop work, show you photos, and get approval before proceeding?

How do you handle jobsite cleanup, and what does "complete" look like?

Ask specifically about nail removal from landscaping and driveway, debris disposal, and a final walkthrough. Get it in writing.

How do you handle supplements?

Supplements are items your adjuster may have missed or undervalued, and they add up. The best contractors have a dedicated team that reviews your estimate line by line before the work begins. A good contractor does it themselves. If the answer is "we'll send it to insurance if anything comes up," by then it's usually too late.

Do you require me to sign an Assignment of Benefits (AOB)?

An AOB transfers your insurance rights to the contractor and often results in the insurance check going directly to them, removing your ability to withhold payment until you're satisfied. A trustworthy contractor doesn't need one. If someone asks you to sign one, ask why.

What is your payment schedule?

Most contractors require a deposit before work begins. The best contractors are confident enough in their work to get paid when the job is done and you're satisfied. Be cautious of anyone requiring large upfront payments. Once they have your money, your leverage is gone.

What warranty do you provide on workmanship, and how do I file a claim?

Materials come with manufacturer warranties, but workmanship warranties are separate and provided by the contractor. Ask how long, what's covered, and how to file a claim. A contractor who can't answer this clearly isn't standing behind their work. The best contractors offer tiered options so you can choose the level of protection that's right for you.