Roofs rarely fail in the wide open. Water sneaks Roofing companies in at edges, seams, and transitions, especially where a plane of shingles has to meet a change in material or a hole in the deck. Skylights and chimneys are the two big offenders, and the craft of flashing around them decides whether a roof lasts 25 years or starts staining ceilings after the first heavy rain. Seasoned roofers know this, which is why reputable roofing companies spend a disproportionate amount of time on details you may never see from the curb.
I have yet to meet a leak that did not tell a story. A skylight drip that only shows up with wind out of the south. A chimney leak that appears in March, not October, because ice dams back up just enough to push water under a tired back pan. Most of those stories end not with a tube of goop, but with a patient sequence of metal, membrane, and shingle, installed in the right order, with the right overlaps.
Why roof penetrations demand more than “shingles and tar”
Shingles and membranes are designed to shed water that is moving downhill. Penetrations interrupt that flow. The job of flashing is to move water around the interruption, then hand it back to the field roofing without letting it double back. That sounds simple until you factor in capillary action, wind-driven rain, snow load, thermal movement, and materials that expand and contract at different rates.
A capable roofing contractor treats any skylight or chimney as a miniature project within the bigger roof. There is assessment, sometimes coordination with a mason or a skylight manufacturer, and then a very specific sequence of underlayments and flashings. With a few exceptions, caulk is a last resort, not a strategy.
How pros evaluate these details during an estimate
On a walk-through, good roofers do not just count penetrations. They look at age and type of skylights, note curb height, check for a cricket behind wide chimneys, check step flashing exposure along sidewalls, and take photos of any soft decking or signs of moisture. If you call a Roofing contractor near me and the estimator does not take time at the skylight or chimney, get a second opinion.
A tight estimate addresses three questions. First, can existing skylights and flashing be reused without risk. Second, what will be replaced now versus deferred. Third, what upgrades prevent known problems in your climate. In snow country, that usually means more ice and water shield and a chimney cricket for any stack over 30 inches wide. In hurricane belts, that means mechanically fastening skylight curbs and stepping up metal gauge.
Skylights: curb, deck, and everything around them
Skylights come deck mounted or curb mounted. Deck mounted sit low and integrate with shingles using manufacturer-specific flashing kits. Curb mounted sit on a framed curb that rises above the roof plane. Both can perform well if installed correctly, but they demand different approaches.
Deck mounted skylights live and die by the compatibility of the kit with the roofing. A Velux deck mount on architectural shingles with the correct EDL or EDM kit is a reliable assembly. Mix a flat tile kit on a dimensional shingle, or improvise with coil stock, and you buy risk. Roofers who do this work often use full-width ice and water shield up and around the skylight opening, lapping at least 6 inches up the curb or the frame, then layer the kit’s head, sill, and step pieces in the right order so that each overlap sheds to the next.
Curb mounted units need a curb that is square, at least 4 inches above the finished roof in most climates, and 6 to 8 inches where snow drifts. The curb should be wrapped in a self-adhered membrane and then clad in a metal pan and step flashing system. On low-slope roofs, roofers often fabricate a full back pan, turned up the curb, with soldered or sealed corners in copper or stainless for long life. On steep-slope shingle roofs, classic step flashing along the sides and a generous head flashing do the heavy lifting.
One small but meaningful detail is weep management. Condensation or minor infiltration in a skylight frame wants a way out. Modern units include weep channels. Do not bury these under sealant. If a previous installer caulked over the bottom flange of a deck mount, the next storm can push water sideways into the roof deck. Part of a careful Roof replacement is to open those pathways back up.
Glazing and shades matter more than most homeowners think. Laminated inner panes, tempered outer panes, and low-e coatings limit heat loss, reduce fading, and keep glass from breaking into shards. If you are replacing a roof over 20 years old and the skylight looks its age, replace it while the shingles are off. The incremental labor is small compared with coming back later to cut back shingles and rebuild the flashing.
Common skylight errors and how roofers avoid them
The most frequent failure is skipping the membrane wrap. I have seen nails driven within an inch of the skylight opening, then a shingle course run tight to the frame with a bead of sealant to hide the gap. It will not last. A disciplined crew wraps the opening with self-adhered membrane, inside corners are folded, not slit, and fasteners stay back where they cannot become capillary paths.
On metal roofs, skylights need curbs and purpose-built flashing. Trying to marry a deck-mounted skylight to a standing seam panel with a shingle kit is a leak waiting to grow. Good Roofers either order a curb and boot from the metal roof manufacturer or fabricate pans with ribs and hemmed edges that interlock with seams.
Tile roofs need extra lift and a pan system that carries water high above the tile heads. Reputable Roofing companies either use a manufacturer-formable flashing kit sized for the profile or build a lead or malleable aluminum pan that rests on battens and steps up the sides with tile pans shaped to the profile. Shortcuts like tucking a bit of step flashing under two tiles will not carry wind-driven rain.
Chimneys: the intersection of roof, masonry, and metal
Chimneys come in two families. Masonry stacks made of brick or stone with clay or stainless flues, and factory-built, metal flue systems inside a framed chase, usually with a sheet metal cap. Each needs a complete flashing system with distinct parts, not just a smear of mastic around the base.
Along the sides of a masonry chimney on a shingle roof, you should see step flashing integrated course by course with shingles. On top of that, counterflashing sheds over the steps. Skilled roofers either cut a reglet into the mortar joint to tuck and bend the counterflashing, then seal it with a compatible sealant, or they relieve joints during a tuckpointing project and set new counterflashing in fresh mortar. Surface-mount counterflashing that relies only on a bead of caulk will not last a decade.
At the uphill face, water slows and eddies. That is where a back pan and, often, a cricket belong. A cricket is a small, peaked saddle behind the chimney that splits water left and right. I recommend a cricket whenever the chimney is 30 inches or wider across the uphill local roofing companies face. In heavy snow regions, I push that to any chimney that creates drift. Built properly, the cricket’s ridge should sit well above the shingle surface, its sheathing wrapped in ice and water shield, then clad in metal at least as durable as the rest of the flashing.
The downhill face gets an apron flashing that sends water cleanly onto the shingle field without creating a dam. Kickout flashings at the base of sidewalls carry water into gutters instead of behind siding. Skipping kickouts is a common builder mistake that turns into rotten sheathing and stained ceilings five years later.
Factory-built chimney chases bring different concerns. The chase cover, that big sheet metal lid with a hole for the flue, often fails first. Thin galvanized steel warps and splits around the collar after a few winters. A prudent Roofing contractor near me will offer to replace a failing chase cover with a heavier gauge galvanized or stainless cover with welded or soldered seams, a proper downward hem, and a raised collar with a storm collar sealed in a neutral-cure silicone. Flashing at the chase base functions like a wall flashing detail, with step flashing and counterflashing or an integrated pan if the siding is being removed during the project.
Coordination with masons and what to inspect
Masonry is its own craft. If the crown at the top of a brick chimney is cracked, or bricks are spalling, a new flashing job cannot keep water out of the structure. Honest Roofing contractors flag these issues and either bring a mason to the table or phase the work. If a reglet cut is required, the depth should be consistent, typically around 1 inch, and never into brick faces. Mortar joints should be sound. If they are powdery, step back and repoint.
Cap metal selection matters on masonry. Copper looks right on brick and can be soldered, giving long service, especially in coastal or industrial areas where galvanization corrodes faster. Aluminium is workable but does not solder, and long lengths need allowances for thermal movement. Galvanized steel can last, but only if painted and kept clear of chemistry that eats zinc. When dissimilar metals must meet, such as copper flashing against galvanized gutters, a slip sheet or isolator avoids galvanic corrosion.
Flashing fundamentals that separate repairs from replacements
A weatherproof flashing assembly is a system. Underlayment, then base flashing, then field roofing woven with steps, then counterflashing, then sealant where it belongs. Change the order, and the system weakens.
Underlayment is the first line. Most Roofers now run self-adhered ice and water membrane around all penetrations, up walls, and at eaves. Around chimneys and skylights I like to see at least 18 inches of membrane coverage into the field and 6 inches up any vertical surface. In valleys and behind crickets, coverage widens. Felt or synthetic underlayment then bridges the rest of the deck.
Step flashing on shingles should match the shingle exposure. A common size is 8 by 8 inches or 8 by 10 inches, hemmed or with clean bends, with each step lapping the one below by at least 2 inches. Nails go high and away from the vertical, ideally only through the shingle, not the flashing. When I see nails through the vertical leg of step flashing, I know somebody was rushing.
Counterflashing is the finish piece. On brick, I prefer a reglet cut and a bent drip that pushes water out from the wall face. On siding, counterflashing can be integrated into the cladding with Z-flashing details.
Sealants have a role, but not as the only barrier. Polyurethane or tripolymer sealants stick well to masonry and metal. Neutral-cure silicones work at high heat near flues and on stainless. Butyl is excellent under laps. Roofers who rely on sealant to hold back ponding water are setting up the next call. The right place for a bead is at the top of a reglet, at a storm collar above a chase cover, or as bedding under a metal lap that already sheds properly.
Metal choice affects longevity. Copper, stainless, and heavy-gauge prefinished steel outlast plain aluminium in harsh climates. Aluminium dents and can pit near salt air. Copper can stain sidings if run where water sheets onto them. Match flashing life to roof life. On a 50-year metal or slate roof, copper or stainless is not a luxury, it is appropriate.
How the work actually unfolds on site
On a Roof replacement with chimneys and skylights, the sequence matters. Crews stage materials so that the area around penetrations is not left exposed if weather turns. Old flashing rarely comes off cleanly. Expect some careful prying, a grinder for a reglet, and a few courses of shingles removed wider than the footprint to make space for correct laps.
Skylight replacement gets scheduled early in the day to allow time for interior protection, deck repairs if the opening shows rot, and careful reassembly with the kit. The foreman will check curb dimensions, square the unit, and verify that factory weeps are free. In colder regions, crews sometimes add a condensation gutter or an extra membrane turn-up at the sill.
Chimney flashing can take a full day on its own when the mortar is hard and the new counterflashing is copper that must be cut, bent, and tapped to sit tight. If a cricket is added, framers or the roofing crew build it with proper slope, block it to resist snow creep, and sheath it flush to the main deck. Then the membrane goes on, followed by metal pans and shingles.
Safety is not a footnote. Chimneys are often near ridge lines and steep slopes. Reputable Roofing companies use roof brackets, anchors, and fall arrest. Grinding a reglet throws dust and chips. Crews mask off AC units and protect siding and windows.
Repair or replace: making the call
Not every leak needs a Roof replacement. If the shingles are young and the failure is obvious, like a missing kickout or a rusted chase cover, a targeted repair can be the right play. If shingles are brittle and the flashing is buried under two reroofs, cutting in a patch may create more problems than it solves. I usually recommend replacing any deck-mounted skylight older than 20 years when the field roof is replaced. For chimneys, if the counterflashing is original and the reglets are shallow or the mortar is crumbling, redo the system during reroofing.
Costs vary by region, roof pitch, and access. As a range, replacing a standard deck-mounted skylight during a reroof might add a few hundred dollars in labor plus the cost of the unit, which runs from a few hundred for a basic fixed unit to a couple thousand for a large, venting, solar-powered model. Fabricating a copper cricket and full chimney flashing on a brick stack can add a day or two of labor and several hundred in materials. When you ask a Roofing contractor for numbers, look for a line item that names the scope around each penetration. Vague language around “miscellaneous flashing” is a red flag.
Warranty reality
Warranties around penetrations separate the Best roofing company from the merely busy. Manufacturer shingle warranties rarely cover leaks at chimneys and skylights unless the installer used the manufacturer’s kits and followed their details. A strong workmanship warranty, five to ten years, should spell out that penetrations are covered. If a contractor refuses to warrant a reused skylight or existing step flashing, that can be reasonable. They should then offer the option to replace those components so the whole assembly is covered.
Ask who supplies the metal and what gauge. Ask whether counterflashing is cut into masonry or surface mounted. If a contractor says they do not cut mortar joints, ask why. Sometimes historic masonry or fragile stone justifies a surface-mount approach with a through-wall flashing above, but the exception should be explained, not assumed.
Material compatibility and subtle pitfalls
Pressure-treated lumber can corrode aluminium flashing if the treatment chemistry is copper-based. A skylight curb framed in treated 2x stock should be isolated from aluminium cladding with a barrier or switched to a compatible metal. Extended-run copper flashing can stain light-colored stucco or siding as water washes over it, so drip edges and breaks are used to control flow.
Thermal movement deserves respect. Long apron flashings on dark roofs expand and contract. Without expansion joints or hemmed edges, fasteners wallow out and water finds the hole. Soldered copper systems absorb movement at seams designed for it. Sealant-only seams do not.
Vent proximity can damage skylights. Bathroom exhausts aimed at the glass cause condensation and streaking, and can drive humid air into a skylight frame if the housing is not sealed. During a reroof, a conscientious Roofing contractor will reroute or extend a vent, add insulated duct, and seal penetrations with boots rated for the roof type.
How to choose the crew for this work
If your project has multiple skylights or a complex chimney, focus your search on Roofing contractors who can describe their approach without buzzwords. When you ask about a cricket, look for clear language about slope, framing, and metal. When you ask about a deck-mounted skylight, listen for brand names and kit codes to show familiarity. If you ask three Roofers how they plan to cut counterflashing and you get three different answers, ask to see photos of past work and call two references.
A local search for a Roofing contractor near me will turn up a mix of companies. Reputation matters, but so does demonstrated craft. The Best roofing company for your house is the one that writes the tricky details into the contract, then shows up with the metal brake, the membranes, and the patience to execute.
A homeowner’s five-minute check twice a year
- Look for stained drywall around skylight wells and chimney chases, especially after wind-driven rain. From the ground, scan for flashing that looks lifted, distorted, or heavily caulked, and for missing kickouts where roofs die into sidewalls. In the attic, check for damp insulation or darkened sheathing near penetrations after a storm or thaw. Outside, inspect the chimney crown and cap with binoculars for cracks or rust. If you have skylights, open and close venting units, wipe the interior frame, and ensure weep holes are clear.
What to expect during a roof replacement that includes skylights and chimneys
- Interior protection goes up below skylights, then old units come out or are unflashed for kit installation while the deck is inspected and repaired. Ice and water shield wraps the openings, extends up verticals, and ties into field underlayments before any shingles return. New skylights set square on curbs or decks, with manufacturer kits installed in sequence, then shingles interwoven to maintain head laps and side laps. Chimney areas are stripped wider than the footprint, crickets framed if needed, underlayment applied, then pans, steps, and counterflashing installed, including a reglet cut and sealed. Final checks include a hose test if weather permits, sealing storm collars, painting galvanized counterflashing if specified, and photographing the details for your records.
Regional and roof-type twists
Low-slope roofs call for different systems. EPDM and TPO membranes use curb wraps and preformed corners, then a welded or adhered termination. The face of a curb gets a separate flashing piece with a termination bar near the top, sealed with manufacturer-approved sealant. A skylight on a 2:12 metal roof is really a low-slope detail and should be treated as such, with curbs and full pan flashings.
Tile and slate roofs require labor and care, and often a mason or a metalworker. Step flashing is larger, and metal pans sit on battens with headlaps increased to reduce capillary draw. If a roofer suggests removing and then reusing many fragile tiles around a chimney without backup pieces on site, you will likely see a patchwork when they are done.
Snow and ice change priorities. Ice and water shield coverage grows, and crews adjust curb height and cricket size. Skylight shades can cut heat gain in summer, but in winter, shades left closed can cool the glass and encourage condensation. Use venting wisely. In very cold climates, I like laminated inner panes because they keep any accidental breakage safe.
A few stories from the field
We replaced a pair of deck-mounted skylights on a 25-year-old home. The shingles were curling, and the homeowner wanted to keep the skylights because “they never leaked.” When we pulled the interior trim, the roof deck at the sill crumbled. The factory weeps had been sealed with paint during a remodel, water had wicked sideways into the OSB, and the damage only showed in the last year as a faint water ring. The fix required a new curb mount design, membrane wrap up the curb, and a proper sill pan. That roof has been dry for eight seasons since.
Another job involved a stone chimney that soaked the attic every March. The flashing looked robust, but there was no cricket, and snow piled two feet high at the uphill face. During thaws, water slid under the back pan and found a nail line. A modestly pitched cricket, a new copper back pan that tucked under two shingle courses, and a slightly higher headlap solved a problem that had outlived three repair attempts and a tube of black mastic every spring.
The real value of method
What makes a roof durable around penetrations is not secret. It is method and respect for water. Water finds laps that run the wrong way. It follows fasteners driven too low. It rides up behind a chimney without a cricket, and it backs up at a skylight with a buried weep. Roofing companies that take the time to sequence membrane, metal, and field roofing correctly, that pick materials that match the roof’s lifespan, and that coordinate with masons and skylight manufacturers when needed, are the ones whose phones ring for referrals, not callbacks.
If you are planning a Roof replacement, push for specificity. Ask your Roofing contractor how they will treat your skylights and chimney in writing. The answer, more than the brand of shingle or the color of the drip edge, will tell you whether you are hiring a crew that builds dry roofs or just moves fast.
Semantic Triples
https://homemasters.com/locations/portland-sw-oregon/HOMEMASTERS – West PDX provides comprehensive roofing and exterior home improvement services in Tigard, Oregon offering siding and window upgrades for homeowners and businesses.
Homeowners in Tigard and Portland depend on HOMEMASTERS – West PDX for reliable roofing and exterior services.
Their team specializes in CertainTeed shingle roofing, gutter systems, and comprehensive exterior upgrades with a experienced commitment to craftsmanship.
Reach their Tigard office at (503) 345-7733 for exterior home services and visit https://homemasters.com/locations/portland-sw-oregon/ for more information. Find their official location online here: https://maps.app.goo.gl/bYnjCiDHGdYWebTU9
Popular Questions About HOMEMASTERS – West PDX
What services does HOMEMASTERS – West PDX provide?
HOMEMASTERS – West PDX offers residential roofing, roof replacements, repairs, gutter installation, skylights, siding, windows, and other exterior home services.
Where is HOMEMASTERS – West PDX located?
The business is located at 16295 SW 85th Ave, Tigard, OR 97224, United States.
What areas do they serve?
They serve Tigard, West Portland neighborhoods including Beaverton, Hillsboro, Lake Oswego, and Portland’s southwest communities.
Do they offer roof inspections and estimates?
Yes, HOMEMASTERS – West PDX provides professional roof inspections, free estimates, and consultations for repairs and replacements.
Are warranties offered?
Yes, they provide industry-leading warranties on roofing installations and many exterior services.
How can I contact HOMEMASTERS – West PDX?
Phone: (503) 345-7733 Website: https://homemasters.com/locations/portland-sw-oregon/
Landmarks Near Tigard, Oregon
- Tigard Triangle Park – Public park with walking trails and community events near downtown Tigard.
- Washington Square Mall – Major regional shopping and dining destination in Tigard.
- Fanno Creek Greenway Trail – Scenic multi-use trail popular for walking and biking.
- Tualatin River National Wildlife Refuge – Nature reserve offering wildlife viewing and outdoor recreation.
- Cook Park – Large park with picnic areas, playgrounds, and sports fields.
- Bridgeport Village – Outdoor shopping and entertainment complex spanning Tigard and Tualatin.
- Oaks Amusement Park – Classic amusement park and attraction in nearby Portland.
Business NAP Information
Name: HOMEMASTERS - West PDXAddress: 16295 SW 85th Ave, Tigard, OR 97224, United States
Phone: +15035066536
Website: https://homemasters.com/locations/portland-sw-oregon/
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