What a storm-only chimney leak is telling you
If your chimney leaks after every storm but stays dry in light rain, you've got a flashing problem. That's the near-certain answer.
Flashing is the metal and sealant that bridges the gap where the chimney passes through the roof. When it's sound, water slides right past. When it fails, wind-driven rain gets behind it and rides straight into your attic.
The reason it only shows in storms is simple. Gentle rain falls straight down and drains off. Storm rain comes in at an angle and gets pushed up under any loose edge.
So the leak isn't random. It's a specific gap that only opens up when the wind and water hit it just right.
The good news: flashing repairs are usually well under a thousand dollars if you catch them early. The bad news: people ignore these for years, and that's when the framing rots.
The usual suspects, ranked
In the field, chimney flashing failures fall into a short list. Let me walk you through them in the order I actually find them.
Number one is counterflashing that's pulled out of the mortar joint. That's the metal cap tucked into a groove in the brick. Mortar shrinks over 15 to 25 years, the metal loosens, and storm wind lifts the edge.
Right behind that is old roofing tar cracking open. Somebody 'fixed' the leak years ago with a bucket of black cement. It dries, alligators, and splits, and now it funnels water instead of blocking it.
Then there's step flashing on the sides of the chimney. If a piece is missing or someone ran it as one long strip instead of interwoven L-pieces, driven rain slips under it.
Wide chimneys have their own issue. Anything past about 30 inches wide needs a cricket, a little peaked diverter on the uphill side. No cricket means water piles up behind the chimney until it finds a seam.
The outliers are cracked chimney crowns and rusted chase covers. Those aren't roof flashing at all, but they read like a flashing leak from inside, so a good diagnosis checks them too.