I had a roofer come two times to repair a single leak. The roofer preferred to use a slow approach to avoid any big repair by using calk which cost $250-$350 (forget which) including renailing some loose shingles the 1st attempt and $100 for the 2nd attempt. After the last night's heavy rain, I still have water coming into my master bathroom closet right where the wall meets the ceiling. This area is quite wet and you can see a light driblet of water slowly rolling down the sheet causing stain streaks. In fact, I can hear light pinging (like water dripping onto metal) as it sounds like it is hitting the metal flange surround the chimney tube in the attic. I can feel a driblet or two coming all the water down on the metal gas fireplace insert too.

The roofer who worked on the leak twice came today and doesn't seem to know where the water is coming from but suggested it might be coming down the chimney through the cap. I am not sure how it happened but the cap is slightly dented causing water to lightly pool up. Another roofer came today and quoted me $1,000 to $1,500 to reflash the entire area where the chimney meets the roof and to remove siding from the chimney to look for water damage. Another roofer also came and was very confident the water is coming in where the roof meets the chimney. He said the water is getting behind the shingles and coming into the house (right above the water damage in bathroom) and then rolling along the backside of the plyroof/frame of the chimney. This makes sense but it doesn't explain the pinging noise I was hearing like dripping from the roof cap. There is also a small hole in the chimney box quite a few feet above the attic floor but I can't see water coming down from that high up. However, what's that pinging noise? He quoted me $550 to reflash that corner of chimney/roof.

I am concerned about dropping another $550 and not resolve the problem. I'd be a bit more comfortable if i didn't hear the pinging of what sounds like water dropping down onto the metal shielding.

Pics -> Image Viewer

 

You have shown pictures of everything but the most important place, the roof penetration of the chimney chase.

You need "step flashing" under every single course (row) of shingles and then a "counter flashing" from the chimney chase (or brick chimney) to cover the step flashing. From your description it sounds as if you may be missing one or the other. If you have a brick chimney then the counter flashing is embedded in the mortar joints and replacing it is a fairly labor intensive 9read costly) endeavor. If the last roofer failed to properly install the step flashing then you could lose quite a few shingles in the process of adding the step flashing.

 

Based on the pictures only, water is pooling around the bottom of the chimney cap & could be entering there but not going in the stack itself. It might be going along the outside of it & hitting the metal plate on the attic floor. That would explain the pinging. If you ca get up there with a hose, test it that way or just have someone caulk around the chimney cap (AKA spark arrestor).

 

I'd remove that cap and have a new one made that bent to the center is higher then the outsides so water would run off not pool up like that.

 

It really sucks that I cannot quote messages.

We had major rain last Friday/Monday (5" on Friday alone) and I noticed a lot of wetness on the attic floor and on the bathroom closet's wall near the ceiling (right under the attic floor corner). The roofer came over Tuesday and did some caulking around the base of where the exhaust cap meets the chimney cap (I think; I am confirming with him) but I am not sure if he did any more caulking. We had more rain off and on including some heavy periods on Thursday and I still heard the pinging noise but the attic floor was completely dry including the shaft. I wonder if he did something to "fix it". I wondered if the leak was from the chimney but I don't see water damage on the outside of the box. If it ran down the shaft it wouldn't enter the attic floor because there is a gap between the shaft and the outer flange. I guess it is possible there is two leaks...

 

Is there a 'clean out' in the cellar or somewhere else? Open it.

 

I agree, a ton of great pictures but not the one that will let us see where the chimney meets the roof line. Is there a cricket on the back side of the chimney? Do gutter meet at the chimney? Is the soffit solid or vented vinyl?

While the cap is holding water, I think that it may contribute to the pinging noises I believe it is unrelated to the leak. I don't see any moisture migrating from the center to the exterior areas inside the chimney. Look for moisture at the fireplace insert or where ever the flue leads too.

So send us a picture similar to the pictures of the chimney cap, but tilt the camera down so we can see where the shingles meet the chimney on all sides as well as from below looking up at the soffit.