What to expect during a roof replacement, step by step

Knowing what a roof replacement actually involves takes some of the stress out of it. Once you have chosen a roof replacement contractor, the job itself tends to follow a predictable sequence, even though the exact pace depends on your roof’s size, pitch, and condition once the old material comes off.

Before the crew arrives

A good contractor confirms the material order, pulls any required town permit, and schedules the dumpster or debris trailer before the first day. This is also when they should walk you through what to move or protect: patio furniture, grills, cars in the driveway, and anything fragile near the exterior walls. Ask what happens with your gutters, AC condenser, and any solar panels if you have them, since those need protecting or temporary disconnection. It is also a good time to confirm a start date window rather than an exact date, since roofers commonly build a few days of slack into their schedule for weather.

Day one: tear-off and inspection

The crew strips the old roofing material down to the decking, which is the plywood or board layer the shingles sit on. This is the loudest, messiest part of the job, and it is also when the contractor gets their first real look at the condition of your roof structure. Soft, rotted, or water-stained decking gets flagged here. A contractor who tells you about a decking problem before covering it back up, with photos, is doing the job right. One who never mentions it either has a very lucky roof or is not looking closely.

Underlayment, flashing, and ice-and-water shield

Once the deck is exposed and any repairs are made, the crew installs a water-resistant underlayment across the whole roof, with a self-adhering ice-and-water membrane along the eaves and valleys where Connecticut winters put the most stress on a roof. New flashing goes in around chimneys, skylights, and anywhere a wall meets the roofline, since old flashing is a common source of leaks even on roofs that otherwise look fine. Drip edge gets installed along the perimeter to direct water into the gutters properly.

Installing the new roofing material

With the roof properly prepped, the finish material goes down: shingles, metal panels, or another product, depending on what you chose. Straight, even shingle lines and properly spaced nail patterns are signs of careful work. Ventilation components, ridge vents and soffit vents, get installed or reconnected here too, since poor attic ventilation shortens the life of any roof, no matter how good the shingles are.

Cleanup and final walkthrough

A thorough crew uses tarps to catch debris as it comes off the roof and runs a magnetic sweep of the yard, driveway, and any garden beds for stray nails before calling the job finished. The final walkthrough is your chance to check the work with the contractor present: flashing looks clean and tight, gutters and downspouts are reinstalled, vents are not blocked, and shingle lines are straight with no exposed nail heads. Bring up anything that looks off during this walkthrough rather than after the crew has left, since it is much easier to fix while the ladders and materials are still on site.

Phase	What happens	Typical duration
Prep	Permits, material delivery, property protection	1-5 days before work starts
Tear-off	Old roofing removed, decking inspected	Morning of day one
Repair	Any rotted decking replaced	Same day, if needed
Underlayment and flashing	Ice-and-water shield, underlayment, new flashing	Day one or two
Installation	New shingles, metal, or other material installed	Remainder of the job
Cleanup	Debris removal, nail sweep, final walkthrough	Last hour of the final day

Ask for a written manufacturer warranty on the materials and a separate workmanship warranty from the contractor covering their labor. The two are different, and a contractor who only offers one is leaving you exposed if an installation error causes a leak down the line.

You can read more about how we evaluate contractors on quality and responsiveness in our methodology, and see the full directory for roofing contractors serving Hartford Metro.