Questions to Ask a Roofer Before You Sign a Contract

Before you sign with any roofer in Connecticut, confirm five things: that they hold an active Connecticut Home Improvement Contractor registration, that they carry liability and workers' compensation insurance, exactly what work and materials the price includes, how decking repairs and other surprises will be priced, and what warranties cover both the materials and the workmanship. Then read the contract itself. Connecticut law requires home improvement contracts to be in writing, signed by both parties, include start and completion dates and the contractor's registration number, and give you a three-day right to cancel. A roofer who answers these questions clearly and in writing is usually one you can trust.

Best Way Roofing is a Wolcott-based roofing contractor led by owner Luis Aguayza, registered under Connecticut HIC #0634957. We are a GAF Master Elite contractor recognized with GAF's 2026 President's Club award, Owens Corning Preferred, and we back our roofs with a 15-year workmanship warranty and more than 400 verified reviews. We answer these questions for homeowners every week, and we think every Connecticut homeowner should ask them of every roofer they consider, including us.

In This Guide

• Questions About Licensing and Insurance: Confirming the basics.
• Questions About Experience and Crews: Who is doing the work.
• Questions About Your Roof's Condition: Repair or replace.
• Questions About the Scope of Work: What the price includes.
• Questions About Materials: Shingles and the full system.
• Questions About Price and Payment: Avoiding surprises.
• Questions About Warranties: Manufacturer and workmanship.
• Questions About the Project Itself: Timing, permits, and cleanup.
• What Connecticut Law Requires in Your Contract: Know your rights.
• How to Compare Two Roofing Quotes: Line by line.
• Red Flags to Watch For: When to walk away.
• Frequently Asked Questions: Quick answers.

Questions About Licensing and Insurance

Start with the basics. If a roofer cannot answer these clearly, the rest of the conversation does not matter.

Are You Registered as a Home Improvement Contractor in Connecticut?

Connecticut requires home improvement contractors to register with the Department of Consumer Protection. The registration number, which looks like HIC followed by seven digits, must appear on contracts and advertising. You can verify it on the state's online license lookup before you sign.

Do You Carry Liability and Workers' Compensation Insurance?

Ask for a certificate of insurance sent directly from the insurance agent. Liability insurance covers damage to your property. Workers' compensation covers injuries to the crew. Roofing is dangerous work, and if an uninsured worker is injured on your property, you could face serious problems.

Will You Pull the Building Permit?

Most Connecticut towns require a permit for a roof replacement. A professional roofer should pull it and schedule any required inspections. Be cautious of anyone who suggests skipping the permit.

Questions About Experience and Crews

How Long Have You Been Roofing in This Area?

Local experience matters. Connecticut roofs face ice dams, nor'easters, heavy snow, and freeze-thaw cycles, and a roofer who works here year-round understands what those conditions require.

Who Will Actually Be on My Roof?

Ask whether the company uses its own crews or subcontractors, who will supervise the job, and who you should call with questions while work is underway. There is nothing wrong with subcontracted crews if they are well managed, but you should know who is responsible.

What Manufacturer Certifications Do You Hold?

Manufacturer certifications, such as GAF Master Elite or Owens Corning Preferred, require contractors to meet standards for licensing, insurance, and training. They also unlock stronger warranty options that uncertified contractors cannot offer.

Can I See Recent Projects and Reviews?

Look for recent work in your area and reviews on independent sites. Patterns in reviews, both good and bad, say more than any single comment. You can see our recent work in our project gallery and read our customer reviews.

Questions About Your Roof's Condition

Before talking about price, make sure the roofer has actually looked at your roof.

Do I Need a Full Replacement, or Can It Be Repaired?

A trustworthy roofer will tell you when a repair makes more sense than a new roof. Ask what they found, how much life the roof has left, and why they are recommending one option over the other. Our guide to roof repair vs. replacement explains how that decision is usually made.

Did You Go Into the Attic?

The attic shows things you cannot see from the roof, such as old leak stains, condensation, mold, and ventilation problems. A thorough inspection includes both. Our roof inspection checklist lists what a complete inspection covers.

Can I See Photos of What You Found?

Photos of damaged shingles, flashing, and attic areas help you understand the recommendation and compare it with other quotes.

Questions About the Scope of Work

Two roofing quotes can differ by thousands of dollars because they describe different jobs. These questions make sure you are comparing the same thing.

• Will you tear off the old roof completely, or install over it?
• How will you inspect and repair the decking, and how will you tell me what you find?
• What underlayment will you use, and where will ice and water barrier go?
• Will you replace flashing at chimneys, walls, and skylights, or reuse the old flashing?
• How will you handle ventilation, and will you check that the attic is properly vented?
• Will you replace pipe boots, drip edge, and ridge vents?
• What happens to gutters, skylights, and satellite dishes during the job?

A detailed answer to each tells you whether you are getting a full roof system or just new shingles. Our guide to how long a roof replacement takes walks through each step of a complete job.

Questions About Materials

Which Exact Shingle Product Will You Install?

"Architectural shingles" is not specific enough. Ask for the manufacturer, product line, and color in writing. Many homeowners choose a GAF architectural shingle line, and you can preview options on our GAF shingle colors page.

Are the Accessories From the Same Manufacturer?

Manufacturer system warranties often require using the manufacturer's underlayment, starter strips, ridge caps, and ventilation products. Mixing brands can limit warranty coverage.

What Wind Rating Will the Roof Have?

Wind ratings depend on both the product and how it is installed, including the number of nails per shingle. Ask what rating your installation will qualify for.

Questions About Price and Payment

The price you sign for should be the price you pay, apart from clearly defined extras. Ask these questions before you agree:

What Exactly Is Included in the Price?

Get a written, itemized estimate that lists tear-off, disposal, underlayment, flashing, ventilation, shingles, accessories, permits, and cleanup.

How Will Decking Repairs Be Priced?

Damaged decking cannot be seen until the old roof is removed. Ask for the price per sheet or per board in writing, and how you will be notified before extra work is done. Our guide to roof decking explains what can come up.

What Is the Payment Schedule?

Understand when deposits and progress payments are due. Be cautious of large upfront payments, especially to companies you cannot verify. Ask whether financing is available if you need it.

Will You Work With My Insurance Company?

If storm damage is involved, ask how the roofer documents damage and communicates with your adjuster. A reputable contractor helps you through the claim but does not pressure you or make promises about what insurance will cover. Learn more about our storm damage services.

For more on what drives roofing prices, see our guide to new roof cost factors.

Questions About Warranties

There are two kinds of roof warranties, and you want to understand both.

Who Registers the Warranty?

Many enhanced manufacturer warranties must be registered by the contractor after installation. Ask who handles it and when you will receive the documents.

What Voids the Warranty?

Ask what could void coverage, such as improper ventilation, mixing accessory brands, or future work by another company.

As a GAF Master Elite contractor, we can offer enhanced GAF warranty options on qualifying roofs, along with our own 15-year workmanship warranty. Our warranty information page explains the options.

Questions About the Project Itself

When Can You Start, and How Long Will It Take?

Ask for an estimated start date and duration. Most residential roofs take one to a few days, depending on size and weather.

How Will You Protect My Home and Yard?

Ask how the crew will protect landscaping, siding, windows, and driveways, and where the dumpster will go.

How Will You Clean Up?

Ask whether the crew uses magnetic sweepers to pick up nails in the yard and driveway, and whether cleanup happens daily or only at the end.

What Happens if It Rains?

Ask how the roof will be protected if weather changes mid-project, especially in Connecticut, where conditions can shift quickly.

What Connecticut Law Requires in Your Contract

Connecticut's Home Improvement Act protects homeowners. Under state law, a home improvement contract must:

• Be in writing and signed by both you and the contractor.
• Contain the entire agreement between you and the contractor.
• Include the date of the transaction.
• Include the contractor's name, address, and registration number.
• Include start and completion dates.
• Include notice of your right to cancel within three business days.



You should also receive a copy of the signed contract. The state's Home Improvement Guaranty Fund may reimburse homeowners up to a capped amount when a registered contractor fails to fulfill a contract, which is one more reason to hire only registered contractors.

How to Compare Two Roofing Quotes

Once you have more than one estimate, compare them line by line rather than looking only at the total. Check that both include a full tear-off, the same type of underlayment and ice barrier coverage, new flashing, ventilation work, and the same shingle quality. Compare decking repair pricing, warranty levels, and who registers the warranty. A quote that looks lower often leaves out items the other one includes, or uses a lower-grade product line. If something is missing, ask the contractor to add it or explain why it is not needed, then compare again.

Red Flags to Watch For

Walk away, or at least slow down, if a roofer:



• Cannot provide a Connecticut HIC registration number or proof of insurance.
• Pressures you to sign the same day or offers a "today only" price.
• Asks for full payment before work begins.
• Shows up door to door right after a storm with no local address.
• Gives a vague, one-line estimate without listing materials or scope.
• Suggests skipping the permit.
• Offers to "take care of" your insurance deductible.

Trust your instincts. A good roofer will give you time to review the estimate and answer every question.

Ask Us Anything

We welcome every one of these questions. If you are planning a new roof, schedule a free roof inspection and we will give you a detailed written estimate, explain your shingle and warranty options, and answer anything else you want to know. Learn more about our roof replacement services or see our FAQs.

Call Best Way Roofing at (203) 527-8149 or contact us. We are based at 102 Wolcott Road in Wolcott and serve homeowners throughout Central Connecticut.

Frequently Asked Questions