Let’s be honest—shopping for a new roof isn’t exactly thrilling.

A new roof isn’t something you shop for every day. It’s high stakes, high cost, and—if we’re being real—hard to compare.

You’re handed two estimates. One is cheaper. One sounds smarter. Both promise peace of mind.

So how do you know who’s telling the truth?

You ask better questions.

Here are the ones that cut through the noise—straight from the contractor's mouth. (Or at least, the ones who should be talking.)

1. “Are You Licensed and Insured to Work in Kentucky?”

Seems obvious. Isn’t always.

Ask to see:
✔ Kentucky roofing license
✔ General liability insurance
✔ Workers’ comp policy

Why it matters: If a contractor slips off your roof in Lexington and isn’t insured, you could be held responsible.

2. “Who Will Actually Be On My Roof?”

You’d be surprised how often the person quoting the job isn’t the one doing the work.

Ask:

• Is your roofing crew local to Lexington or Central KY?

• Do you use subcontractors or W-2 employees?

• Who manages the project from start to finish?

Trustworthy roofers don’t vanish after the handshake.

3. “What Roofing Materials Will You Be Using?”

Not all shingles are created equal. Especially in Kentucky’s four-season weather.

Ask:

• What shingle brand and grade?

• Do you use ice & water shield (especially in winter)?

• What underlayment and flashing are included?

A high-quality roof in Lexington needs to handle heat, hail, wind, and ice. Cheap shortcuts won’t last.

4. “How Will You Address Ventilation?”

Lexington summers are humid. Without good attic ventilation, your roof—and your energy bills—will suffer.

Ask:

• Will you inspect my attic?

• What’s your plan for intake and exhaust ventilation?

Smart ventilation is silent savings.

5. “What’s Your Clean-Up Process After the Job?”

Nobody wants to find rusty nails in the driveway six weeks later.

Ask:

• Do you tarp landscaping?

• Will you use magnetic rollers?

• Is clean-up in writing?

A great Lexington roofing contractor leaves your property better than they found it.

6. “What Happens If Something Goes Wrong?”

Even the best roofers in Kentucky have callbacks. What matters is how they handle them.

Ask:

• What is your workmanship warranty?

• What if I see an issue a year from now?

• Who do I contact for service?

If their answer is “Don’t worry about it,”—worry.

🔎 Bonus Question: “Do You Understand Insurance Claims?”

This matters especially in Lexington, where storm damage is common.

At UnderCover Roofing, we spent 15 years managing claims before ever replacing a roof. We know how the process works from the inside out—and we use that knowledge to protect your claim and your time.

Final Thought

A roof is a big deal. It protects your home, your family, and your future.

If you’re hiring a roofer in Lexington, KY, make sure they’re not just good at installation—but also communication, cleanup, and care.

And if you want someone who already knows the questions you haven’t thought of yet?

We’re here.

UnderCover Roofing
With You Through the Storm
Serving Lexington and Central Kentucky with integrity, transparency, and claim expertise.

📞 Ready for your free expert roof inspection?
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