The call
An Enfield homeowner had water showing up inside after rain. The chimney had recently been worked on by a chimney contractor, so the roof was the last thing they suspected. No storm, no missing shingles you could see from the driveway. That is the most common kind of roof leak we get called for in Enfield, and it almost never comes from the shingles themselves.
What we found on the roof
We went up on July 30, 2026 and walked the whole roof, then checked the deck from the attic side. Three problems, in order of how much water each one was letting in:
**1. New chimney flashing installed on top of the shingles.** The chimney work was recent, and the lead flashing was laid over the shingles instead of stepped under them. Flashing only works when each piece is woven under the course of shingles above it, so water running down the roof passes over the metal. Laid on top, the flashing does the opposite: water runs down the shingles, hits the lead, and goes straight underneath it into the roof. The sealant bead along the top edge had already cracked open. This was the biggest source of the leak, and it was brand new work.
**2. Exposed, rusted nails through the apron flashing.** Where the roof meets the siding, two nail heads were driven straight through the flashing and left bare. Both had rusted. A rusted nail head is a small funnel: water follows the shank down through the metal and into the deck.
**3. A nail through the face of a shingle.** One nail had been driven through the exposed part of a shingle instead of under the course above it, with no sealant over the head. Same problem, smaller scale.
From the attic we could see nail points coming through the plank decking and water staining directly under the chimney, which told us where to check from above and confirmed we had found every path water was taking.
Chimney contractors are not roofers
This comes up on Enfield roofs more than it should. A chimney crew relines or rebuilds a chimney, then dresses the base with flashing the way a mason would, on top of whatever is there. It looks finished from the ground. But the roof-to-chimney joint is a roofing detail: step flashing woven into the shingle courses, counter flashing let into the mortar joint over it. When the flashing goes on over the shingles, the first heavy rain finds its way in. If your chimney was worked on recently and you now have a leak near it, that is the first place we look.
What it was doing inside
From the attic, the damage was easy to see: the plank decking and the rafter directly under the chimney were stained dark where water had been running down them after every rain. That is what a "small" roof leak looks like from below, and it is why we always check the attic and not just the roof surface.
Left alone, this does not stay a stain. Wet wood in a closed attic grows mold, the decking softens and starts to rot, insulation packs down and stops working, and the air that mold and damp wood give off moves down into the rooms below. Homeowners often notice a musty smell before they ever see a water mark, and that damp, moldy air is a health problem, not just a smell. The CDC links indoor mold exposure to coughing, wheezing and asthma attacks, and in people who are sensitive or already have lung disease, to serious lung infections and conditions like hypersensitivity pneumonitis. A roof leak over a bedroom is a breathing problem waiting to happen. The fix on the roof stops the water. Catching it early is what keeps a one-visit repair from turning into replaced decking, new insulation and a remediation bill.
Why exposed nails leak
A nail belongs under the shingle above it, where the next course covers the head. When a nail is driven through the exposed face of a shingle or through a piece of flashing and left bare, rain hits the head directly. The nail rusts, the hole around it opens up, and water runs down the shank into the wood. It is a slow leak, which is exactly why it does so much damage before anyone notices. On this roof the nails and the chimney flashing were doing the damage together.
What we did
Same visit, about an hour on the roof:
- Corrected the chimney flashing so water sheds over it, not under it, pressed it tight to the brick and sealed the top and bottom edges.
- Capped both exposed nail heads on the apron flashing with sealant.
- Sealed the nail heads and collar on the plumbing vent boot.
- Capped the exposed nail at the eave.
- Photographed every spot before and after so the homeowner has a record of exactly what was done.
Written quote before any work
You get a written scope and an exact price before tools come out, and roof repair inspections in Enfield are free. No surprises on the invoice.
Warranty
Every repaired area carries our 1-year leak-proof warranty, in writing. If the same spot leaks again, we come back and fix it at no charge.
If your Enfield roof is leaking
Thompsonville, Hazardville, Enfield Center and Scitico are full of roofs from the 1990s and early 2000s, and chimney flashing laid over the shingles and exposed nails are the two things we find most often on them. If you have a stain on a ceiling or water in the attic, book a free roof repair inspection in Enfield or read how we find and fix roof leaks and repair flashing.