Homes age unevenly. Windows leak before shingles curl, fascia rots while the ridge still looks decent, and a storm can force decisions you planned to make next year. When you are weighing a window installation service and a roof replacement, the calendar matters as much as the contract. Sequencing those projects well protects your home from avoidable water damage, reduces rework, and can save thousands in scaffolding, labor overlaps, and warranty headaches. I have seen neighbors replace beautiful windows only to scuff, bend, or reflash them six months later when the roofers arrived. I have also watched roofing crews cut perfect new step flashing, then fight with window contractors who showed up after the fact and tore it out. The fix is not complicated, but it is deliberate.

This is a practical guide based on field experience, not a brochure. It will help you decide what to do first, when to combine tasks, how to stage the work by season, and how to evaluate the right roofing contractor and window partner so materials, flashing, and warranties align.

Why sequencing matters more than most homeowners think

A roof and windows share critical water paths. At every wall plane that intersects a roof, you have a layered system: housewrap or sheathing, window pan flashing, side and head flashing tapes, step flashing at the sidewall, occasional kick-out flashing at the eave return, and sometimes counterflashing or trim. Disturb the order of those layers and you create capillary paths that pull water inward. Do the work in the wrong sequence and you force one trade to undo the other’s work.

The roof is the outer umbrella; windows are penetrations in the vertical shell. Proper waterproofing depends on “shingle fashion” layering. That means upper layers lap over lower layers so gravity works for you. When you change windows after the roof is complete, especially around dormers or sidewall transitions, you often break the shingle-fashion sequence unless both contractors coordinate the flashing tie-ins. If they do not, you end up with caulk doing a job that metal and membranes should handle, which fails early.

There is also a logistics angle. Roofers need access from above. Window installers need clear, plumb openings and stable trim planes. If the fascia, soffits, or rake boards are rotted, both trades cannot set crisp lines. And if a gutter system is ancient or poorly pitched, rainwater can overshoot and drench fresh sealant at window heads. I have seen new windows in a coastal town leak during the first nor’easter, not because of the window, but because step flashing and kick-out flashing were never coordinated when the roof went on the previous season.

The simple rule: roof first when there is shared flashing

Assuming the roof is due within 12 to 24 months and your windows intersect a roof line or sit beneath active roof planes, schedule the roof replacement first. The reasoning is straightforward. Roofers will:

Strip shingles and old flashing down to the deck and wall intersections. Inspect and replace damaged sheathing, fascia, and sometimes framing at eaves or rakes. Install ice and water shield at eaves and valleys, synthetic underlayment on the field, and step flashing at walls. Set new kick-out flashings where roofs die into vertical siding.

With that foundation in place, your window crew can integrate their pan flashing and head flashing tapes into a system that already sheds water predictably. If you reverse it, you either trap old flashing under new window tapes or you ask roofers to pull and reset fresh window details, which is not their domain and not in their bid.

There are exceptions, which I will get into, but as a baseline, if you are comparing a roof replacement of aging shingles with visible granule loss and windows with drafts, and there is any shared flashing, do the roof first.

When windows should lead

You might lead with windows if your roof is in good shape, has life left, and your window issues are urgent. For example, single-pane sliders that sweat all winter, wood sashes with visible rot, or failed double-pane units with fogging that obscures a view. If the roof shows minimal wear and there are no roof-to-wall flashing conflicts, windows can go first without regret. This is common on simple gable homes with clean wall planes and no dormers or returns.

Another good reason to start with windows is a large interior renovation. If you are redoing drywall, interior trim, and paint, the dust and staging happen inside. Roofing brings vibration and occasional fastener pops at ceilings, but it does not usually affect interior finish quality if you time the window install carefully. In that situation, confirm that exterior trim and siding around the windows do not rely on roof flashing, then proceed.

The last case is project phasing due to budget. If financing allows only one project per year, you pick the greater risk first. A leaking unit or a patio door that will not lock is a security and water concern that ranks above a roof with five years left. If you can document no roof-to-wall flashing dependencies, schedule windows now and set expectations with your roofer for courtesy flashing checks later.

Reading the home: practical field diagnostics

Most homeowners can spot missing shingles or cracked glass. The more useful questions sit in the overlaps. Here is how I walk a house when advising on sequence.

Start at the eaves. Look at gutters. Are there drip edges correctly tucked over the gutter back flange, or do you see a gap that allows capillary draw behind the fascia? If the drip edge is wrong, your fascia and soffits often tell the story. Soft spots, peeling paint, or wasp nests around damp wood indicate chronic moisture. When that is present, the roof is a priority because it controls the water path along the entire eave line, which also protects window heads below.

Move to sidewalls where roof planes meet walls. Do you see step flashing layered under the siding, or is there a long continuous L-flashing? Long continuous L is a red flag in older roofs. If water runs behind it, it has no weep path. Proper step flashing works in individual pieces overlapped with each shingle course. If you have continuous L-flashing, plan on redoing it during the roof job and do the roof before window replacements in that area. Also check for kick-out flashing at the bottom of those step runs. If downspout stains or rot exist at the base of the wall near the eave return, the lack of a kick-out is part of the problem. Again, roof first.

Look at dormers. Dormers are detail-heavy: sidewall step flashing, front wall apron flashing, and sometimes headwall flashing at the rear. If your windows sit in dormer walls, they and the step flashing are interdependent. You do not want a window crew cutting into step flashing to fit new trim. Roof first here almost always wins.

Inspect the attic on a sunny day with a strong flashlight. Dark stains on the back of roof sheathing along nails is old moisture. A window leak often shows up as staining on a wall stud bay or at the top plate, not on the roof sheathing. If the attic sheathing is stained or the insulation is damp along the eaves, that is a roofing problem. If the wall bays below windows are stained, that is a window or wall flashing issue.

From inside, feel for drafts around window sashes on a breezy day. A strong draft with sound roof planes suggests failed window seals or poor installation. Combine that with outdoor checks to sort urgency.

Integrating trim, siding, and insulation into the timing decision

Many homes pair a roof replacement with exterior siding work. If you are also planning to re-side, the stack order becomes siding, windows, and roof working together, but the specific flow is walls first at the rough stage, roof during the mid stage, and finishing together. In a typical fiber cement or engineered wood re-siding project, you strip old cladding, inspect sheathing, update housewrap, set new window flashings with proper pan and head detailing, then the roofing contractor ties step flashing into those wall layers. After that, siding and trim wrap it up. That sequence maintains shingle-fashion water shedding and gives both trades clean surfaces to work with.

If you are adding exterior insulation like 1 inch to 2 inches of foam, the trim and flashing depths change. Window bucks and extension jambs might push the window toward the exterior plane. That modifies head flashing and kick-out geometry. It also changes gutter offsets and drip edge positions. This is where the best roofing company and an experienced window installer collaborate on details before anyone shows up. A half-day preconstruction meeting with drawings and a tape measure saves days of field improvisation.

Seasonality and weather windows

Climate influences sequence more than people admit. In northern zones, roofs prefer late spring through early fall. Windows can be done almost year-round if you prepare for short openings and keep interior heat stable. In the Southeast and Gulf regions, hurricane season complicates roof tear-offs, but windows with proper DP ratings and installation can proceed with less exposure. In the mountain West, morning frost and afternoon winds change schedules, so plan for flexible crew days.

I avoid roof tear-offs in the late fall if overnight temperatures will drop below freezing and rain is likely on tear-off day two. Underlayment products are good, but adhesive performance and crew safety degrade. Windows in those months are fine, especially insert replacements that do not disturb exterior cladding. If you must reflash full-frame windows in winter, use tapes and sealants rated for cold application, and heat the substrates with a safe infrared lamp so adhesion meets spec.

Pollen season in some areas creates another nuisance. Sticky tapes and airborne pollen are a poor mix. If your house is under a canopy of pines, you can plan around the heavy yellow weeks to get cleaner bonds.

Cost overlap and how to avoid paying twice

Homeowners hate paying for the same access twice. I keep a short mental ledger for overlapping tasks so the roof replacement and window installation service do not duplicate charges.

Scaffolding and lifts are the biggest shared expense on multi-story homes. If dormer windows or upper-story units need full-frame replacement, coordinate so the roofer’s scaffolding stays for a few extra days under an agreement, or the window contractor brings it in first and the roofer rents at a discount. Most roofing contractors prefer pump jacks or roof jacks with planks, but many are happy to share scaffold towers near steep wall sections if liability is clear and the equipment is rated. On a three-story Victorian with a steep mansard, combining access saved a client about 2,000 dollars.

Dump fees are another. If both projects happen within a week, a single 20-yard container can handle shingles, old windows, trim, and flashings with some planning. Mixed debris pricing varies, but one container instead of two is often a few hundred dollars saved.

Flashing and trim labor can overlap. For example, if the roofer replaces rotten fascia and rake boards, ask them to leave primed but unpainted trim for the window crew to integrate with exterior casings. That avoids cutting fresh paint twice. Similarly, if the window installer discovers rotten sheathing during a full-frame replacement, coordinate a same-day patch from the roofer if the area touches roof planes. Two crews for one hour each costs less than a return trip for one crew.

Warranty traps and how to sidestep them

Manufacturers have become stricter about installation details. Asphalt shingle warranties often require specific underlayment types, starter strips, nailed patterns, and properly installed flashing. Window manufacturers care about level, plumb, and square, but they also require proper pan flashing, head flashing with drip caps, and integration with weather-resistive barriers. If a later trade disturbs those elements, the finger-pointing starts.

Ask both companies, in writing, how their warranties interact with adjacent work. A reputable roofing contractor will state where their flashing responsibilities end at window or siding interfaces, and how they expect those elements to remain. The best roofers also specify that any later removal of step flashing voids leakage coverage along those runs. Window contractors should specify that their warranty assumes a working weather-resistive barrier and proper roof flashing at adjacent planes. If either company waves off these questions, keep looking. Search terms like roofing contractor near me or best roofing company will yield a flood of options, but dig beyond the ads. Look for project photos that show the sequencing you need, not just finished glamour shots.

I also encourage homeowners to photograph critical details during the work. Not to police the trades, but to have a record of what is concealed. Take photos of pan flashing at sills, head flashings before trim, and step flashing courses as the shingles go on. If a warranty claim arises, those images help everyone remember the sequence and materials, and they can save time.

Material choices that change the plan

Some materials are forgiving; others demand exact sequencing.

Cedar or redwood shingles on sidewalls often pair with copper step flashing. Copper wants to be integrated once, not bent back and forth. If you have cedar sidewalls and plan new windows, replace or repair the windows first, then do the roof and copper in one run. If the copper already exists and is in good shape, leave it and plan window inserts, not full-frame replacements that would disturb the sidewall layers.

Tile and standing seam metal roofs complicate the story. Tile flashing is rigid and layered. Pulling it later to redo window head flashings is expensive and risky. With standing seam, the pan and cleat details at sidewalls are shop-bent and site-hemmed. If a standing seam roof is coming, schedule it with window work coordinated or done first so the metal fabricator and window installer agree on offsets and counterflash details. This is a place where the best roofers truly shine, not because they are the cheapest, but because they understand how to lock in the order of operations months ahead.

Synthetic stucco (EIFS) or hardcoat stucco around windows is another special case. Once stucco is cut, you need a qualified stucco contractor to tie back in. If your roof must be replaced and you have stucco-clad dormers, convene three parties: roofer, window installer, and stucco pro. Decide whether to run new head flashings under the stucco or create a visible metal head flashing with a small reglet cut. Plan the sequence so wall patches are minimal.

Energy, comfort, and ROI timing

From an energy perspective, window upgrades often deliver comfort faster than pure cash savings suggest. On paper, a roof replacement with the same attic insulation does little for utility bills unless you air seal and top up insulation. Windows, by contrast, can reduce drafts and improve mean radiant temperature in rooms you use every day. A homeowner in a 1980s colonial told me their family room went from unlivable on windy days to comfortable after replacing six leaky casements with modern units, even though the furnace runtime only dropped about 5 percent. They valued the comfort more than the bill.

If you plan to sell within three years, curb appeal and inspection points matter. A roof nearing end-of-life will appear on any buyer’s report. Failed window seals will too, but buyers often accept a credit for a few windows more readily than for a whole roof. That calculus can tilt the sequence toward the roof first to protect sale value. If budget forces one project, ask your agent and weigh the local market. In some neighborhoods, new windows with black exterior frames and clean trim transform the look and attract buyers even if the roof has a few years left. There is no one answer; the right call blends risk, aesthetics, and timing.

How to choose the right partners for a combined project

Credentials matter, but so does attitude toward coordination. When you interview roofing companies and window installers, listen for how they talk about the other trade. A pro who routinely blames “those window guys” or “those roofers” will likely push problems onto you. A collaborative contractor will talk sequencing, flashing transitions, and who handles what.

Ask each for:

One project reference where they coordinated with the other trade on roof-to-wall flashing around windows or dormers. A sample scope statement that defines responsibilities at intersections, including kick-out flashing and head flashings. Proof of insurance and a willingness to name the other trade as additional insured during overlapping workdays.

These are mild tests. The best roofing companies and window firms will have answers on hand and a calm tone about coordination, not defensive posturing.

Practical schedules that work in the field

Here is a schedule that has worked on dozens of homes with mixed roof and window needs, assuming shared flashing:

Week 1: Preconstruction. Final measurements, order windows and roofing materials, confirm lead times, and hold a coordination call. If special flashings or metals are needed, shop-fabricate now.

Week 2 to 4: Lead time buffer. Use the gap to address permitting if required, HOA approvals, and color decisions for shingles and window exteriors. If gutters are part of the scope, choose profiles early so drip edge and gutter apron details match.

Week 5: Roofing mobilization. Tear off, repair sheathing, install ice and water, underlayment, and new step flashing at sidewalls. Install kick-outs and drip edges. Do not install final siding or trim changes yet at those walls.

Week 6: Windows. Full-frame replacements in areas that touch roof planes first, then inserts elsewhere. Integrate pan flashings with the existing WRB and coordinate head flashing with the roofer’s counterflashing where relevant. Inspect each opening for plumb, square, and proper fastener schedules. Low-expansion foam around frames, then backer rod and sealant.

Week 6 to 7: Roofing wrap-up. Shingle to final courses, integrate with window head flashings where needed, set ridge vents, rehang or adjust gutters, and verify kick-outs direct water into gutters cleanly. Window team installs exterior trim and paints or coats as appropriate.

Week 8: Punch list and documentation. Walk the home with both trades. Photograph concealed flashings that are still partially visible, test hose at suspect transitions, and collect warranties and material datasheets.

That may look slow to some, but it keeps the critical overlaps tidy and leaves room for weather surprises.

Edge cases and tough calls

Historic homes with plaster walls and weight-and-pulley windows are delicate. Dust from plaster work and the need for custom storms or sashes can push window work into cooler months when humidity is lower. If the roof is marginal, a short-term roof repair like sealing exposed fasteners, replacing a few shingles, or adding a temporary membrane at a valley may buy a season for careful window restoration. Do not rush either trade on a historic facade. Small mistakes cost big in character and dollars.

Condominiums and townhomes add HOA layers. Often, the association controls roof work while owners manage windows. If the roof replacement is on the HOA’s five-year plan, but you need windows now, request the HOA roofing specs and share them with your window installer. Good specs will note step flashing details and underlayment types. Ask the roofing company who maintains the HOA roofs to comment on window sequencing. It is in their interest to avoid future conflicts.

Insurance-driven replacements after hail or wind create another timing dilemma. Carriers typically set deadlines for roof claims. Windows might not meet damage thresholds, or the adjuster might miss subtle seal failures. If the roof is a covered loss and the windows are not, do the roof first to secure the claim. Then, while the roofer is onsite, ask them to assess flashing around suspect windows and to document issues. Some carriers will reconsider window components if clear evidence appears during tear-off.

What to expect from a quality roofing contractor during sequencing

When you search roofing contractor near me, you will find a wide range of outfits, from two-person crews to well-established roofing companies with full project teams. Regardless of size, a quality roofer brings:

A written scope that lists all flashings by location, not just “flash as needed.” A plan for protecting existing windows and trim during tear-off, including ground protection, window wraps, and a cleanup schedule that prevents nails or debris from damaging glass or sills. Clear communication on daily start and stop times, weather holds, and temporary dry-in measures if rain threatens mid-project.

The best roofers rarely shy away from coordination. They will meet your window installer, mark lines on the walls to indicate where counterflashing will land, and agree on who sets the kick-out dimensions. They will also tell you when to avoid window installs, such as on a day when they are stripping above that plane. That candor prevents broken glass, bent screens, or scratched frames.

Red flags that signal trouble

Two signals worry me more than any online review. First, a contractor who dismisses flashing details with “we just caulk that.” Sealant is a backup, not a primary water management strategy. Second, a bid that excludes all decking repair as “extra” with no unit pricing. Roof tear-offs often reveal bad sheathing near eaves or valleys. Without unit prices in the bid, change orders can balloon. Window installers sometimes discover rot too. Ask both trades for unit prices on sheathing and framing repair. Good companies have them printed.

If a contractor refuses to provide insurance certificates or balks at naming the other trade as additionally insured for overlapping days, they may not be comfortable working alongside another crew. That is not an automatic no, but it is a caution flag.

Putting it together: how to make the final call

Most homes fall into one of three buckets.

If your roof is 18 to 25 years old, shows curling, missing tabs, or widespread granule loss, and you have any roof-to-wall intersections near windows, schedule the roof replacement first. Choose a roofing contractor who respects sequencing and flashing integration. Then, replace windows, starting with those near the roof planes, and finish with stand-alone openings.

If your roof is mid-life with only minor issues, but your windows leak, stick, or show failed seals, and there are no roof-to-wall interfaces complicating things, prioritize the windows. Use a window installation service that documents flashing layers and anticipates a future roof change. When you do replace the roof later, ask the roofer to review and preserve those flashings.

If you have complex interfaces, materials like stucco, tile, or metal, or plan to re-side, treat the project as an integrated exterior envelope job. Bring the best roofing company you can find, a window specialist with full-frame experience, and, if relevant, a siding or stucco professional into one planning session. Set the sequence in writing, then execute without gaps between trades so no one leaves a half-finished water path exposed to weather.

I will close with a short story that captures the stakes. A client with a 1920s bungalow replaced eight windows in March to tighten the home before allergy season. The dormer sidewalls met a low-slope porch roof. The window crew did fine work, but they tied head flashings into a brittle old rolled roof that should have been replaced two years earlier. April storms arrived, and water found the path between the new head flashings and the failing roof membrane. The repairs were not catastrophic, but they cost time, stained ceilings, and frayed nerves. Six weeks later, a new roof with proper step and apron flashing fixed the system. If we had reversed the order by a month, there would have been no drama.

Good sequencing is not flashy. It is the quiet discipline of doing things in residential roofing companies the right order so the home works as a system. Find roofing contractors and window partners who value that discipline. Ask clear questions, make them talk to each other, and pick dates that work with your climate. You will spend fewer dollars on rework, enjoy a tighter, drier home, and protect warranties that matter when storms come through.

The Roofing Store LLC (Plainfield, CT)

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Name: The Roofing Store LLC

Address: 496 Norwich Rd, Plainfield, CT 06374
Phone: (860) 564-8300
Toll Free: (866) 766-3117

Website: https://www.roofingstorellc.com/

Email: [email protected]

Hours:
Mon: 8:00 AM – 4:00 PM
Tue: 8:00 AM – 4:00 PM
Wed: 8:00 AM – 4:00 PM
Thu: 8:00 AM – 4:00 PM
Fri: 8:00 AM – 4:00 PM
Sat: Closed
Sun: Closed

Plus Code: M3PP+JH Plainfield, Connecticut

Google Maps URL:
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The Roofing Store is a customer-focused roofing contractor in Plainfield, CT serving Windham County.

For residential roofing, The Roofing Store helps property owners protect their home or building with experienced workmanship.

Need exterior upgrades beyond roofing? The Roofing Store LLC also offers siding for customers in and around Plainfield.

Call (860) 564-8300 to request a project quote from a professional roofing contractor.

Find The Roofing Store LLC on Google Maps: https://www.google.com/maps/place/The+Roofing+Store+LLC/@41.6865305,-71.9184867,17z/data=!3m1!4b1!4m6!3m5!1s0x89e42d227f70d9e3:0x73c1a6008e78bdd5!8m2!3d41.6865306!4d-71.9136158!16s%2Fg%2F1tdzxr9g?entry=tts

Popular Questions About The Roofing Store LLC

1) What roofing services does The Roofing Store LLC offer in Plainfield, CT?

The Roofing Store LLC provides residential and commercial roofing services, including roof replacement and other roofing solutions. For details and scheduling, visit https://www.roofingstorellc.com/.

2) Where is The Roofing Store LLC located?

The Roofing Store LLC is located at 496 Norwich Rd, Plainfield, CT 06374.

3) What are The Roofing Store LLC business hours?

Mon–Fri: 8:00 AM – 4:00 PM, Sat–Sun: Closed.

4) Does The Roofing Store LLC offer siding and windows too?

Yes. The company lists siding and window services alongside roofing on its website navigation/service pages.

5) How do I contact The Roofing Store LLC for an estimate?

Call (860) 564-8300 or use the contact page: https://www.roofingstorellc.com/contact

6) Is The Roofing Store LLC on social media?

Yes — Facebook: https://www.facebook.com/roofing.store

7) How can I get directions to The Roofing Store LLC?

Use Google Maps: https://www.google.com/maps/place/The+Roofing+Store+LLC/@41.6865305,-71.9184867,17z/data=!3m1!4b1!4m6!3m5!1s0x89e42d227f70d9e3:0x73c1a6008e78bdd5!8m2!3d41.6865306!4d-71.9136158!16s%2Fg%2F1tdzxr9g?entry=tts

8) Quick contact info for The Roofing Store LLC

Phone: +1-860-564-8300
Facebook: https://www.facebook.com/roofing.store
Website: https://www.roofingstorellc.com/

Landmarks Near Plainfield, CT

• Moosup Valley State Park Trail (Sterling/Plainfield) — Take a walk nearby, then call a local contractor if your exterior needs attention: GEO/LANDMARK
• Moosup River (Plainfield area access points) — If you’re in the area, it’s a great local reference point: GEO/LANDMARK
• Moosup Pond — A well-known local pond in Plainfield: GEO/LANDMARK
• Lions Park (Plainfield) — Community park and recreation spot: GEO/LANDMARK
• Quinebaug Trail (near Plainfield) — A popular hiking route in the region: GEO/LANDMARK
• Wauregan (village area, Plainfield) — Historic village section of town: GEO/LANDMARK
• Moosup (village area, Plainfield) — Village center and surrounding neighborhoods: GEO/LANDMARK
• Central Village (Plainfield) — Another local village area: GEO/LANDMARK