A new roof is one of the biggest checks you will ever write for your home, and the contractor you pick matters as much as the material going on top. A good roofer delivers a roof that lasts decades. A bad one delivers leaks, excuses, and a second bill to fix the first job. These five questions separate the two before you sign anything.
- Are you licensed and insured? This is the non-negotiable first question. A legitimate roofing contractor carries general liability insurance and workers compensation, and holds whatever license your state or locality requires. Ask to see the certificate of insurance and confirm it is current. If a contractor gets defensive about this question, walk away. Uninsured roofers leave you exposed if a worker gets hurt on your property or your home gets damaged mid-job.
- Can you show me recent local work and reviews? Experience matters, but local experience matters more. A contractor who has roofed homes in your area understands your local weather, building codes, and permit process. Ask for addresses of recent jobs you can drive past, plus a short list of references you can call. Then check their online reviews yourself. A pattern of complaints about communication or cleanup tells you more than any sales pitch.
- What exactly does your quote include? The cheapest quote is rarely the best quote, because quotes hide different things. A complete roofing quote should spell out the shingle or material brand and line, underlayment type, whether old roofing gets torn off or roofed over, flashing replacement, ventilation work, permit fees, cleanup, and disposal. Get every quote in writing with the same scope so you are comparing like with like. Vague one-line quotes are where surprise charges live.
- What warranties come with the job? There are two warranties on every roof and they come from different parties. The manufacturer warranty covers the roofing material itself, often 25 years to lifetime depending on the product tier. The workmanship warranty comes from the contractor and covers installation errors, which cause most early roof failures. Two to ten years is typical for workmanship. Get both in writing, and be wary of anyone promising a lifetime workmanship warranty they cannot possibly back up.
- What is the timeline and payment schedule? Ask when the crew starts, how many days the job takes, and what happens if weather delays it. On payment, never pay the full amount upfront. A common fair structure is a modest deposit of 10 to 30 percent, a progress payment when materials arrive or tear-off is done, and the balance on completion after you have inspected the work. Anyone demanding full payment before lifting a shingle is a red flag.
Watch for the classic red flags too: door-to-door “storm chasers” who appear after every hailstorm, high-pressure tactics pushing you to sign today, cash-only deals with no paperwork, and bids far below everyone else. Any one of these is reason enough to keep looking.
Once you have a contractor you trust, the next question is budget. Tyler Roofing Company’s guide to average roof replacement cost breaks down 2026 prices by material and home size so you walk into every estimate with real numbers. Going in informed is the best defense against inflated quotes and the best way to spot a genuinely good deal.
The right contractor welcomes hard questions. Ask all five, compare two or three written quotes, and you will end up with a roof done right the first time.
Author bio: Tyler Roofing Company helps homeowners understand roofing costs and make confident replacement decisions, with research-backed guides on materials, pricing, and contractor selection.
