I'm having a leak problem around my chimney (where the chimney goes through the roof in my attic). I had the flashing replaced and it still leaked. Subsequently I had a Mason inspect the chimney. He did some minor re-pointing and applied water resistant silicon. However, he said the chimney and cap were in good shape (the home is only 15 years old). I had a different carpenter/roofer take another look at the flashing and they noted some areas on the copper flashing that should have been soldered, but had not been. They did the soldering and a couple days later we had 8 hours of heavy rain. The good news is the leaking was much less then previously experienced, but the bad news is there was still some leaking. Basically a few beads of water forming at the area where chimney goes out of the attic and streaming down. Not heavy, but steady.

I this point I don't know if it is still a problem with the flashing or if it is saturating trough the bricks. The new counter flashing goes up from the roof about three feet so if its saturation, the water really has to travel quite far. This is quite frustrating.

Any thoughts/advice appreciated. Photo attached

 

Difficult to comment based on pic provided. Need pics close up to chimney and showing all 4 sides.

 

I know this thread is a few months old, but I had a similar issue over the past year. Had what I figured was a flashing breach although it looked in decent shape to my untrained eye, but a roofer pointed out some areas that he would approach differently. I also had some relatively minor areas of cracked mortar joints.

First thing I did was to re-point the worst of the cracked mortar. I'm no mason but it was pretty easy (got to buy an angle grinder which is fun to use!) and looks pretty good. I wanted to apply a waterproofer next, but it was fall and we had so much rain that by the time I had a nice dry week the temps had dropped below the recommended application temperature so I had to wait.

In the meantime I hired a reputable roofer to re-flash the chimney. This was done in February and while it helped slow down the amount of water infiltration, I still had leakage during heavy rains. Finally a few weeks ago I had a week of drying time for the bricks and the temps warmed up enough for me to apply the waterpoofer to the chimney (I used solvent-based ChimneySaver since I knew that a similar product had already been applied many years ago.) Next I applied ChimneySaver Crack and Joint Sealant to any small fine cracks that didn't warrant re-pointing.

We've had 2 major rainstorms since I did that and I'm declaring victory - no leakage as far as I can tell.

My chimney is only slightly larger than yours. I bought 1 gallon of the waterproofer and it wasn't quite enough for the recommended 2 applications - I got one good coat on followed by a lighter second coat, so I recommend buying more than you think you might need.