Most homeowners buy one, maybe two roofs in a lifetime. That inexperience is why roofing attracts both excellent long-standing local companies and crews that follow storms across three states. The questions below are not about catching anyone out. They are about finding out quickly which kind of company is standing on your driveway.
"Did you get on the roof, and can I see the photos?"
An inspection done from the ground with binoculars is a sales call. A real inspection means walking the field of the roof, checking the valleys, and looking at every penetration: plumbing boots, the chimney flashing, the step flashing where a roof meets a wall, and any skylights. Ask for photographs. Any competent roofer takes them on a phone as a matter of routine, and a company that cannot produce them did not look closely.
"What did the attic look like?"
Half of roofing problems are diagnosed from underneath. Daylight through the deck, dark staining on the sheathing, matted or damp insulation, and rusted nail tips all tell you where water is getting in and where warm moist air is condensing. A roofer who never asked to see the attic has skipped the cheapest and most informative part of the inspection.
Attic ventilation deserves its own question. An underventilated attic bakes the shingles from below and shortens their life significantly. If the proposal does not mention intake and exhaust ventilation at all, ask why.
"Is this a repair, an overlay, or a tear-off?"
An overlay lays new shingles on top of the old layer. It is cheaper and faster, it is legal in many jurisdictions for a single existing layer, and it is almost always the wrong long-term choice. You cannot inspect or repair the decking underneath, the new shingles run hotter, and the next roofer has to remove two layers. Most manufacturers also shorten warranty coverage on overlays.
If a tear-off is quoted, ask what happens if the crew finds rotten decking. There should be a stated per-sheet price for replacement plywood in the contract. Without it, you are exposed to whatever number gets quoted on the day the roof is open.
"What underlayment and what ice barrier?"
The shingle brand gets all the attention, but the layer under it does much of the work. Synthetic underlayment has largely replaced felt and holds up better if the roof sits exposed for a day. In cold climates, a self-adhering ice and water barrier along the eaves is what prevents ice dam leaks, and code often requires it to extend a specified distance inside the exterior wall line. Ask how far up the roof it goes, and ask for it in the valleys too.
"Is the flashing new?"
Reusing old step flashing at a wall or a chimney is a common shortcut, and it is where roofs leak. New roof, old flashing, water in the dining room in year three. The proposal should say new flashing explicitly. So should the line about the plumbing vent boots, which are cheap and fail before the shingles do.
"Who is doing the work, and are they insured?"
Many roofing companies subcontract installation. That is normal and not a problem in itself, but you want to know it up front, and you want a current certificate of general liability and workers compensation insurance sent to you directly by the insurer or agent, not a photocopy from the salesperson. If an uninsured worker is hurt on your roof, that can become your homeowners policy's problem.
Check the license requirements in your state as well. Some states license roofers, some leave it to the county, and some do not regulate it at all.
"What does the warranty actually cover?"
There are two warranties. The manufacturer covers the shingles, and that coverage is often prorated and sometimes contingent on the installer being certified and on the full system being from one manufacturer. The contractor covers workmanship, and this is the one that matters, because most early roof failures are installation errors. Five years of workmanship coverage is a reasonable floor. Ten or more from a company with a long local history is meaningfully better.
On storm chasers
After a hail event, companies you have never heard of will canvass the neighborhood offering to handle your insurance claim and waive your deductible. Waiving a deductible is insurance fraud in many states, and a company that offers it is telling you how it does business. Prefer a contractor with a permanent local address and a history you can look up.
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