Skylights, replaced when it's smart — not twice.
The best time to touch a skylight is while the roof is open. We replace aging units during reroofs, cut brand-new skylights into roofs that never had them, and fix the leakers — documented with photos, quoted line-item in writing.
Should skylights be replaced during a reroof?
Almost always, yes. Skylights and asphalt roofs age on similar timelines, and swapping a unit while the roof is open costs a fraction of a standalone replacement later — you pay for the skylight and modest labor instead of a second roofing project. The new flashing kit integrates with the new underlayment, which is where leak protection actually lives.
That's why every Bailey reroof estimate on a home with skylights includes a line item for replacing them — priced in writing, your call to accept or skip. About the only time we recommend keeping an existing unit is when it's genuinely young: a skylight installed in the last few years can usually be re-flashed into the new roof safely.
What does Bailey do with skylights?
Three things, all documented in CompanyCam from first photo to final walkthrough:
- Replace during a reroof — on a recent Centennial hail claim off South Jasper Court, we replaced both skylights while installing a CertainTeed Presidential IR roof. The insurance scope covered the skylights alongside the shingles because we documented them with the roof — our second project for that homeowner, a real-estate agent with Keller Williams DTC.
- Cut in new skylights — on an Aurora reroof on South Evanston Street, the crew sawed two brand-new openings into the deck, framed the curbs, and flashed the units into the new roof system in the same build. Rooms that had never seen daylight got it in one day.
- Repair the leakers — flashing failures, cracked seals, and clogged weep channels are repairable without buying a new unit. A free inspection with photos tells you whether yours is a repair or a replacement before any money changes hands.
What does a skylight cost?
It depends on when you do it, which is the honest answer most websites skip. Replacing an existing skylight during a reroof adds the cost of the unit plus modest labor, because the roof is already open and the crew is already there. A standalone replacement on a roof we're not working on costs more — it's a small roofing project of its own. A brand-new cut-in costs the most, since it includes opening the deck, framing the curb, and finishing the interior light shaft. Every option gets a written line-item price with your free inspection, so you're comparing real numbers, not ranges off the internet.
The honest version
If your skylight is under five years old and sealing well, we'll tell you to keep it and re-flash it — replacing it would be spending your money for no reason. And if a leak is just failed flashing, we'll quote the repair, not a new unit. A third of what we're called about turns out to be the cheaper fix.
Skylight questions, answered.
Should I replace my skylights when I replace my roof?
Almost always, yes. Skylights and asphalt roofs age on similar timelines, and replacing a unit during a reroof costs far less than a standalone project later — the roof is already open. New flashing kits also integrate with the new underlayment, which is where leak protection actually comes from. We quote it as a line item on every reroof estimate where skylights are present.
Can you add a skylight where there has never been one?
Yes. We cut in new skylights, ideally during a roof replacement — on a recent Aurora reroof we cut two brand-new openings into the deck, framed the curbs, and integrated the flashing with the new roof in the same build. Standalone cut-ins on an existing roof are possible too; they cost more because they include opening the roof and finishing the interior light shaft.
My skylight is leaking — does it need to be replaced?
Not always. Many skylight leaks are flashing failures, cracked seals, or debris-dammed weep channels — repairable without replacing the unit. But an older unit that fogs between panes or has a brittle acrylic dome is usually worth replacing outright. A free inspection with photos tells you which one you have.
Do skylights make a roof more likely to leak?
A properly flashed modern skylight is not a leak risk in normal service. Manufacturer flashing kits, ice-and-water membrane at the curb, and correct integration with the underlayment have made the leaky-skylight reputation largely obsolete. The leaks we see almost always trace to aged flashing, failed seals on decades-old units, or skylights reused through too many roofs.
Will insurance cover skylights damaged by hail?
Frequently, yes. Hail that damages a roof often damages skylights too — cracked domes, fractured glass, and dented flashing belong in the claim scope alongside the shingles. On a recent Centennial claim we documented the skylights with the roof, and insurance covered replacing both during the reroof. We meet the adjuster on the roof and scope it line by line.
Roof coming up? Get the skylights priced with it.
One inspection covers both. Free, documented with photos, written quote with skylights as their own line item — your call from there.