The leak at the skylight is usually not the skylight

Skylights earn their reputation as leakers in a place that rains half the year, but most of the time the unit is innocent. The metal flashing kit around the curb, the seals, and the shingles upslope of it are what actually fail. Seven months of water running at every joint finds the weak one eventually.
How do you tell what failed?
Water inside the light shaft or staining the drywall ring around it is the usual sign. A roofer reads it by where the water shows: flashing failure wets the downhill side first, a failed unit seal fogs or drips from the frame itself, and a cracked dome is obvious from the ladder. Condensation inside a double-pane unit means the seal is gone; that is a replacement, not a repair.
Repair or replace?
Flashing kits and seals are repairable on a sound unit. Fogged glass, cracked acrylic domes, and twenty-year-old units are not worth reflashing; the new unit goes in with new flashing and the problem ends. If a reroof is on the schedule anyway, skylight swaps belong in the same job, because every skylight gets reflashed when the field around it opens up.
What about moss around the curb?
Moss colonies love the uphill side of a skylight curb, where needles collect and the dam holds water against the flashing. Clearing it and keeping it clear is part of why Portland skylights last or do not. When a leak shows up at a skylight, the moss picture on the whole slope is worth asking about in the same call.
What does the roofer need from you?
Which room it drips into, whether the glass is fogged or just the frame weeps, and roughly how old the unit is if you know. Photos from inside help; nobody needs you on a ladder.
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Other services

Roof repair
Leaks, lifted shingles, failed flashing, and moss damage traced to the real entry point.

Roof replacement
Full reroof from the deck up, material options for the wet season, permits handled where required.

Roof inspection
Condition checks for sales, insurance renewals, and roofs that are simply getting old.

Moss removal
Moss and algae removal done the way shingles survive it, plus treatment that slows the return.

Emergency repair
Active leaks, tarping, and storm damage triage when the roof cannot wait for a dry week.

Storm damage
Wind, limb strikes, and hail damage documented for insurance and repaired by local roofers.

Gutter services
Cleaning, repair, and replacement for gutters that have to move serious water for half the year.

Metal roofing
Standing seam metal that shrugs off moss, needles, and seven months of rain for decades.

Skylight repair
Leaks, failed flashing, and fogged units diagnosed and fixed, or swapped during a reroof.

Flat roof repair
Membrane leaks, ponding, and drain problems on low-slope residential and commercial roofs.

Cedar shake
Shake maintenance and honest conversion advice for the Portland area's aging cedar roofs.

Commercial roofing
Membrane repair, restoration, and replacement on flat and low-slope commercial buildings.