Quick answer: the questions to ask a roofing contractor before signing anything cover five areas — licensing, insurance, who actually does the work, money, and warranty — and a good contractor answers all fifteen below without flinching. The point isn’t to interrogate anyone. It’s that the answers a legitimate roofer gives are specific and checkable, while the answers a bad one gives are vague, rushed, or come with pressure to sign today.
We sit on the contractor side of these conversations every week across Anne Arundel, Howard, and Montgomery counties, so we’ll do something slightly unusual: for each question, we’ll tell you what a good answer sounds like — including ours. Use this list on us and on everyone else quoting your roof. This piece is part of our larger guide to hiring a Maryland roofing contractor.
Licensing and insurance: the disqualifying round
1. What’s your MHIC license number?
In Maryland this is question one, and it’s pass/fail. Every contractor doing roofing work on an existing home needs an active MHIC license, and you can verify the number yourself in two minutes — our step-by-step MHIC lookup guide shows exactly how. A good answer is a number, offered instantly. Ours is MHIC #85703. Anything else — “we work under a partner’s license,” “roofing doesn’t need one” — ends the interview.
2. Can you send me your certificate of insurance?
You want proof of two coverages: general liability insurance (protects your property) and workers’ compensation (protects you if someone gets hurt on your roof). A professional roofing contractor emails a current certificate of insurance the same day, direct from their agent if you ask. Vague reassurance — “we’re fully covered” with nothing in writing — is how homeowners end up personally exposed when an uninsured worker falls off their roof.
3. Are you certified by the shingle manufacturer you’re quoting?
Manufacturer certification (GAF Certified, CertainTeed ShingleMaster, Owens Corning Preferred) means the crew has been factory-trained on that roofing system and — more importantly for you — can register enhanced warranties that ordinary installers can’t offer. We hold GAF certification and CertainTeed ShingleMaster status. Certification is not a substitute for the MHIC license; it’s the layer on top.
4. How long have you been in business, and where are you based?
Longevity matters less than locality: a roofing business with a real local address and years of local roofs has a reputation to protect and will still exist when a warranty claim surfaces in year six. Be careful after storms — this is exactly the question out-of-state operators dodge. A good answer includes an address you can find on a map.
The work itself: who, what, and how
5. Who actually does the work — your crew or subcontractors?
Either model can produce a good roof, but you deserve a straight answer, because it changes who’s on your property and whose insurance applies. If subcontractors are involved, ask whether they’re covered under the contractor’s policies and who supervises them. The red flag isn’t subbing — it’s a salesperson who can’t tell you who’s showing up Monday.
6. What exactly is included in the written estimate?
A detailed written estimate should itemize the shingle brand and line, underlayment, ice-and-water shield, drip edge, flashing work, ventilation changes, tear-off and disposal, and permits. “New roof — $14,000” is not an estimate; it’s a number. When two quotes are far apart, the line items are almost always where the difference hides — one includes new flashing and code-required ventilation, the other doesn’t.
7. Will you replace the flashing, or reuse it?
Flashing — around the chimney, in the valleys, along walls and skylights — is where most roof leaks actually start. Reusing old flashing is a classic way to shave a quote and hand you a leak in year three. A good contractor tells you what gets replaced by default and prices the chimney and skylight work explicitly.
8. What happens if you find rotten decking?
Nobody can see the roof deck until tear-off. What you’re listening for is a unit price in writing — per sheet of plywood replaced — before work begins, plus photos of any decking they replace. The scam version is a too-low quote that “discovers” thousands in surprise deck work mid-job, when you have no roof and no leverage.
9. How will you handle ventilation?
Attic ventilation is the least glamorous item on this list and one of the most important: bad ventilation cooks shingles from below in Maryland summers, feeds winter condensation and ice dams, and can void a manufacturer warranty. A contractor who measures your intake and exhaust and explains the plan is thinking about your roof as a system. One who says “we’ll match what’s there” may be repeating a mistake the original builder made.
10. Do you handle the permit, and will this meet code?
In most Maryland counties, a full replacement needs a permit, and the contractor — not you — should pull it, because the permit holder answers to the inspector for building codes. Requirements vary by county, so the specifics belong in the contract. A contractor who suggests skipping the permit to save money is volunteering to cut corners you can’t see either.
Money: schedule, contract, and pressure
11. What’s the payment schedule?
Reasonable structure: a modest deposit, maybe a progress payment on material delivery, and the balance after the work passes your walkthrough. Maryland law limits what home improvement contractors can collect up front, so a demand for half or more before a shingle moves is both a legal problem and a business-health signal — solvent roofers don’t need your money to buy your materials.
12. What does your contract say about changes, cleanup, and property damage?
Read for four things: how change orders get priced and approved in writing, magnetic-sweep cleanup for nails, protection for landscaping and driveways, and who repairs anything the crew damages. Good contractors put all of it in the contract unprompted. If it’s not written, it didn’t happen.
13. Can you give me local references from the last year?
Ask for recent, nearby jobs — then actually call one or two, and ask the question that matters: “did anything go wrong, and how did they handle it?” Every roofer eventually has a problem job; the good ones are distinguished by what happened next. Recent online reviews serve the same purpose if the volume is there.
Warranty: the part everyone skips until it matters
14. What are the two warranties, exactly — and who stands behind each?
Every new roof carries two separate warranties: the manufacturer’s warranty on the roofing material itself, and the workmanship warranty on the installation, which comes from the contractor. Most roof failures in the first decade are installation failures — which means the workmanship warranty is the one you’ll actually use, and it’s only as good as the company behind it. Get both in writing, with years and coverage spelled out.
15. Will you register the manufacturer warranty, and is an enhanced warranty available?
Certified installers can register enhanced manufacturer warranties that extend coverage well beyond the standard version — but registration isn’t automatic, and some contractors simply never file it. Ask who registers the warranty, when, and what confirmation you’ll receive. It’s a two-minute task that homeowners discover was skipped only when they file a claim years later.
The 15 questions at a glance
| # | Question | The answer you want |
|---|---|---|
| 1 | MHIC license number? | A number you verify yourself (ours: #85703) |
| 2 | Certificate of insurance? | Current COI — liability + workers’ comp — sent same day |
| 3 | Manufacturer certified? | Named certification (GAF, CertainTeed) you can confirm |
| 4 | How long in business, based where? | Real local address, checkable history |
| 5 | Your crew or subs? | Straight answer + whose insurance covers them |
| 6 | What’s in the estimate? | Itemized: materials, flashing, ventilation, tear-off, permits |
| 7 | Replace or reuse flashing? | Replacement by default; chimney/skylights priced explicitly |
| 8 | Rotten decking policy? | Per-sheet price in writing, photos of what’s replaced |
| 9 | Ventilation plan? | Measured intake/exhaust, not “match what’s there” |
| 10 | Permit and code? | Contractor pulls it; specifics in the contract |
| 11 | Payment schedule? | Modest deposit, balance after your walkthrough |
| 12 | Changes, cleanup, damage? | All in the contract, unprompted |
| 13 | Recent local references? | Names you can call — including a job that had a hiccup |
| 14 | The two warranties? | Manufacturer + workmanship, both in writing with terms |
| 15 | Warranty registration? | They file it, you get confirmation; enhanced option explained |
Frequently asked questions
What are the most important questions to ask a roofing contractor?
If you only ask three: the MHIC license number (verify it yourself), the certificate of insurance (liability and workers’ comp), and the split between the manufacturer warranty and the workmanship warranty. Those three eliminate the majority of bad outcomes before a contract is signed.
How can you tell a good roofer from a bad one?
Specificity. Good roofers give checkable answers — license numbers, insurance certificates, itemized written estimates, per-sheet decking prices, named references. Bad ones give reassurance and urgency: “fully covered,” “sign today for this price.” The pressure to skip verification is the tell.
What should a roofing estimate include?
Shingle brand and product line, underlayment and ice-and-water shield, drip edge, flashing scope, ventilation changes, tear-off and disposal, decking unit price, permit responsibility, payment schedule, and both warranties. If quotes differ by thousands, compare line items — the cheap one is usually missing something you’ll pay for later.
Is it rude to ask a contractor for proof of insurance?
No — it’s normal, and legitimate contractors expect it. We’d rather send a certificate of insurance than compete against uninsured operators quoting 30% less. Any contractor offended by the request is telling you something useful.
How much deposit should a roofer ask for?
Modest — Maryland home improvement law restricts large upfront collections, and healthy companies don’t need your cash to fund your job. Balance due after completion and your walkthrough. Treat “half down today” as a red flag regardless of how good the price looks.
What is the 25% rule for roofing?
It’s a code concept: when more than a quarter of the roof needs work, replacement of the larger section often comes into play rather than patching. We wrote a full breakdown in our 25% rule guide — worth reading before an insurance-related repair conversation.
Ask us all fifteen
Genuinely — bring the list. We’ll give you the license number to verify, the insurance certificate, the itemized estimate, and the warranty terms in writing, and if your roof doesn’t need replacing yet we’ll tell you that too. Get in touch here or call (443) 233-1119. Family-owned, GAF Certified, CertainTeed ShingleMaster, MHIC #85703.
Talk to a Maryland roofer who tells it straight
Free inspection, photos of what we actually find, and an honest written estimate — whether the answer is a $600 repair or a new roof.
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