What "roof flashing" exactly did they replace? What other work did they do on your roof, as typically one cannot just replace roof flashing?

Show pictures of your house, and roof, and also where the leaks occur.

sorry i meant to put *the flashing around our chimney.

I went ahead and added some photos to the post. my roof only leaks around the chimney.

I see old, rusted flashing. Where is the replacement flashing?

Thats one of the photos they emailed after the most recent visit. i think the photo is just poor quality. ill attach another that i took of the one side that constantly leaks

Andie-

Your latest photo looks like a better job, but that first photo still looks like rusted flashing to me. Unless that is a "before" shot, I'm wondering if they replaced all of the flashing. Have you been up on the roof to look at it yourself?

As someone who has dealt with my own share of roof leaks in the past, I can tell you that water can move laterally in surprising ways. So, just because you have leaking on one side of the chimney does not mean that is the side where the water is getting in. That's why I would want to be sure all the flashing was replaced.

Finally, I'd ask them exactly what they did to install the flashing and how the whole thing was specifically sealed so that rain does not simply hit the shingles and get under them. It doesn't look to me like they did anything to the shingles adjacent to the chimney, so it's not clear to me that you couldn't have unseen problems under those shingles allowing water to move laterally and get in. Below is a video on roof flashing repair showing a much different approach than what your photos show. I'm suggesting that maybe all they did was slap some new flashing up against the side of the chimney, caulk like crazy, and hope that fixed it. If you watch the video, it will help educate you to ask informed questions of them and not let them try to talk over you.

Chimney flashing repair

I am wondering if it is leaking somewhere other than the flashing. How is the cement on top of the chimney itself Could water be running down the brick and coming through there. There just might be something else going on, and it may not be the flashing at all.

If they "fixed" the flashing, but badly, I would expect the leak to move around. Are you *sure* there's no small leak in the roof itself? I've seen the edges of nails pop through shingles above, nails peeking out just barely beyond the nailing flange, small pinholes etc cause leaks. They are a total pain to find but easy to fix once you do.

The one roofer they had said twice that it was the brick/mortar and i needed a masonry guy to come out and that the cracks in crown were causing the leaks. So I had a masonry company look at everything and they said it’s not bad at all and it would be a waste of money to redo anything bc it’s in decent shape right now. Then the owner of the roofing company came out the next time and said no it’s not the mortar/crown whatever. Also it appears the water is coming in between the chimney and our ceiling where they butt up. There’s no water inside our chimney at all. Hopefully this answers some questions thanks for replies. I can add more photos if that helps. from what i can tell they did new step flashing. the leak is still one main area but it has moved bc now its coming in at the front of my chimney as well.. so currently theres 2 spots where its leaking. i dont know that theres not another spot leaking but they did a ”roof inspection” that i paid for so i would assume thats something they shouldve mentioned? how do i move forward? thanks everyone!

Well, the water that is coming out in front of the chimney is running from higher up, so you need to look higher up on that chimney, to find the leaking spot. I did see a crack on the cap in one of your pictures. Maybe its time, to get someone new there to check it all out, since the ones you have had, dont seem to know how to fix it. I know its a roof, but, can you somehow get a picture of the back side of that chimney. Water comes in up above, and then finds a spot to leak out. It could even be higher up on your roof, itself.

And a good way to determine whether the problem has anything to do with the condition of the chimney above the flashing is to get a piece of plastic sheeting (visqueen) which can be draped over the entire chimney, and held in place with a wrap of duct tape. The bottom of the plastic can be trimmed to shape with scissors. This will make the chimney waterproof and confirm whether the leak is coming from the chimney or elsewhere. Of course, for safety reasons, the chimney should not be in active use while you do this experiment. But you don't need to wait for rain: you can create a shower with a garden hose.

I went up on the roof today and took these photos, hopefu hopefully this helps. ill call another roofing company and see if i can get some other opinions. thanks!

The chimney bricks and mortar appear to be in pretty good shape, but you have some significant cracks visible in the chimney cap material and water could be migrating through them. You can test this with the plastic wrap experiment I described above.

Try the water test. Some of the flashing looks ok, but, appears to be gaps on the bottom of the sides..Its hard to tell, if there is caulk in there. Wrapping that chimney, especially the top, should be able to tell, if its coming from the roof, or the top of the chimney

If they could not fix the leak after 4 times, its time to get your money back and find a different roofing company. Take him to small claims court if you do not get your money back.

I noticed the apparent gap between the bottom of the flashing and the shingles. I am no expert, but I don't see how that could possibly be right. Caulk can't be relied upon to seal such a gap, can it? Shouldn't the shingles have been taken up, and step flashing installed on all sides of the chimney?

I had a similar problem where the roof of the one story addition joined to the side of the 2 story house. Two roofers tried more caulking/tar without success - only the 3rd who did remove shingles and redo the waterproofing/ flashing solved the problem.

Looks precisely like our “leak”. After having it recapped and re-flashed, continued having the problem.

Then our chimney cleaner sealed the brick. Problem fixed. It reappears every few years after a particularly heavy wind-driven rain, and he reapplies the waterproofing,