The gutter below that window shows to be full of leaves in your picture. Thats sure not helping anything. It needs to be cleaned. It could very well be the window that is leaking, and running down into the vestibule. You also have a chiminey up there, has anyone checked the flashing on it? It could be leaking and water always runs down the rafters, and finds a place to come in. Can you get into your attic? If so, get up there with a good light, and check around chiminey, and look around a bit, for water stains.

Thanks cat. I'd like to have a someone knowledgeable look at it? What type of place would you recommend calling? I feel like maybe it's too big for handyman? Roofing contracters aren't calling me back and my current roofer days it's not a roofing job.

Not a pro but i see a lot of valleys in the area above the entry. They can often be leakers if not properly done. Did the roofer use any leak shield membranes in the valleys? I do believe shingles have to be laid out a certain way in valleys to prevent leaks

I would want a roofer. They are capable of making sure flashing is right etc. If it turns out to be the window, then, you would need a window installer. The bottom right in the picture, of that window, looks a bit suspect to me too. I would also make sure those gutters are clean and not backing up underneath the roofing shingles. Full gutters can cause a lot of leaks, and I see a lot in that small area of the one under the window, that I can see.

I've asked him about a water test and he poo-pooed the idea. Frankly I think he's ghosted me. I called him in early March when I noticed water again and he said he'd contact me when the weather was warmer. He finally did come out in late May and caulked more and told me to keep an eye on it and let him know. I kept letting him know when it was leaking and finally called again now that we're in August. He told me he'd stop by the next day but that was a week ago. I'm trying to be persistant since we're going to be moving into fall soon, but I think it's becoming clear I need to find someone else.

Lots of sources there. Brickwork above the door, lack of upper gutters, overshooting roof water, an on.

I think I would get a good GC out there and offer to pay them for an evaluation. As WoW says there are a lot of potential things in that area that could be a problem.

IMO a competent roofer should know proper flashing regardless where it's located. Principles of flashing applies to windows and doors same as roof penetrations. There's several potential suspects in the pictures but one is bad workmanship. There's no reason for tying gutter into the valley and there's no prescribed way of doing it due to difficulty in flashing it. That gutter should stop 12-24 inches before intersecting valley. Who's fault is it? Everyone that installed gutters,flashing or shingles and every contractor that has cleaned gutters can share blame but the roofer above them all should spot it before getting out of his truck.

Call in a masonary contractor to check the chimney and the recently installed flashing (by your loyal roofer)

I'm not sure if I'm reading the pics right. But it looks like in the first pic the brick is darkened in the upper right of the arch of the door, and in the bottom pic it looks like that might be the inside of the door where the paint has come off? If so, you might need to get someone in to check the masonry. It almost looks like there is a shadow up the brick wall from the door arch too, but not sure if that is the photo or me, lol.

I'd start by removing the plaster around the door (and maybe the ceiling too) to check the structure for damage, and to help locating where the water is coming in.

Sometimes the problem may be identified from the outside, but often someone is just guessing. Seeing the structure opened up on the inside, although more expensive and messy, provides direct access to the problem areas.

Do you have Nextdoor where you live? Unless you live in a very rural area, I'm not understanding what's so hard about getting a roofer out. There are several roofers in my contact list who will come out and look at roof/leak issues. I've had my roof repaired by at least two of them, and also received good advice about drying things out inside.

If those two couldn't come, then I would check Nextdoor and search for roofers.....the ones with a lot of solid recommendations.

A handyman worth his salt can find the source of leak. Using a thermal camera or thermometer while it's raining isn't rocket science.

Investigating a leak like this is like solving a mystery. The good news is water runs down hill. The bad news is water runs a long way and ruins a lot in its course. Start at the top.

You need a general contractor with a lot of years of experience, another roofer, a chimney rebuilder or a really good carpenter. Be prepared for tear out. This one doesn't look like it has a simple solution. There are lot of factors at play. Start with the chimney and work your way down.

I bet you can smell the wet plaster inside the house.

When it rains again, get the brightest flashlight you can find and methodically start investigating the attic. Look for anything that glistens or reflects light. Listen for drops hitting something. Put your hand all around the fireplace and see if it comes away wet. Chimneys are notorious for flashing failures. Your roofer may have replaced the chimney, but that doesn't mean he flashed it properly. That's the place to start. Then, work your way down.

No one has mentioned the exterior stucco. Stucco has a lifespan. When it joins another material, you have expansion and contraction at different rates. That makes for a water intrusion highway.

You could have a leaking window, too. Another water favorite.

Ask your neighbors for a referral for a general contractor or highly qualified carpenter. Somebody in the neighborhood has done a big project in the last few years. Don't be afraid to knock on doors. It's the best way to find competent contractors. See if you can find another roofer to come take a look. Be willing to pay for their time. You may want to call out a chimney specialist, too. Given the age of the structure, you may have flashing failures. They can be very helpful.

Hopefully, the structure hasn't been compromised. But, this will not go away on it's own.

Remember, good contractors are busy for a reason. They are in demand.

Thanks for all the suggestions so far. I spent the past week or so dialing the phone and setting up appointments. I had a good contractor/handyman come out today. He's done some good carpetntry work for me before and at least he's got contacts to help once a cause or causes can be narrowed further. He agreed to take out the ceiling and get the wet things removed so we can potentially visualize more from the interior as a starting point. At one point, I called Anderson Windows to ask about what a potential replacement window could look like and they put me in touch with one of their certified contracters which happens to be a roofing, siding, window contractor so maybe they will also have some ideas tomorrow when they stop by--they are from about 45 minutes away rather than in town.

I at least feel like there is something happending to help get to the bottom of this.

People above have mentioned the gutter. Techically it is angled away from the corner and drains at the opposite end of the house. The contracter I had out today mentioned it seemed a little odd that there wasn't an end cap on it since it was the higher end of the gutter. It was raining a little today and some water was draining the reverse way--not a lot though.

I was home yesterday morning and I had another contractor out to look at my window. He looked in my attic, at the window, and also pointed to the gutters and flashing. He though I needed to do a "water test" and take a hose and carefully spray each areas. I was looking online for long rigid hose extension which I thought I probably could do.

Shortly after he left, the roofer who I haven't heard from in in a month showed up and I noticed he was up on the roof and he said he caulked a few more areas and suggested the next step was a water test.

I was looking out the window this morning and noticed one of the areas he caulked was not along the wall but actually on the shingles themselves along the valley. Would it have been better for him to do the water test before caulking shingles. If the leaking is gone, is this in anyway an acceptable solution for a new roof?

Caulking does not replace the flashing or properly installed roofing material. It is really designed as an extra precaution and really no roof should have to rely on caulking, period.

I had posted early on that valleys are often trouble spots if not properly done. You have a lot of valleys, gutters and odd angles meeting in that area. I think a rubber roof underlayment needs to be used in many of those areas

Thanks Anna--the roofer did use a rubber type underlayment in that area, but I suppose even one errant nail hole through that membrane could cause a leak.

Can someone please confirm for me where the leak is showing? I see no evidence of it in the ceiling and only directly above the door.

Do we have any ceiling damage below the valley?

This looks more like masonry issues to me. What is the wall construction?

Thanks Windows on Washington. The water leak is coming from the above the ceiling. This week I had the ceiling torn out and the wet insulation above the celing removed so the area can dry out and also provide a way to see inside. The wettest area seems to be coming from directly under the area in the black circle--particularly under that verticle brown post.

I had another handyman also come by to take a look and he was able to look up on the roof as well. He sprayed water on the roof farter up from that area and allowed water to flow down. No water was sprayed on the walls and the leak was recreated. He is thinking it is the flashing in this area.

I hope this is what the roofer will also think and agree to redo that area. I supposedly have a warranty but what good is it if the roofer who offers it doesn't agree.

Roof to wall connections are where most of the leaks will show. That and penetrations in the roof. Sounds like some step, apron, or counter flashing is missing or done improperly.

thanks for keeping us updated.

I snapped a couple more photos this morning. First is the ceiling of the entryway. The door to the left is the front door to outside and the door to the right is the door to the main hall/foyer of the house.

The next too are some close ups of the areas I noticed water on the roof when the area above this was sprayed with water. Water drains from above and some water drains along the red line in the second photo. The window guy and handyman have mentioned that could an area with faulty flashing.

The third photo shows the corner by the window. When water drains off the roof, some does run along the blue squiggle in the blue circle. The paint is peeling a little there. I wonder if some sort of additional overhang or flashing might be good to direct the water further out onto the roof below?

I called and emailed the original roofer yesterday letting him know things were opened up and asking about the water test. He did email back late late night saying that the heat was delaying other other projects and it would be next week. I understand he's busy and weather is unpredictable too far out, but it's annoying because I don't hear from him for weeks and then all of a sudden I get call asking if I'm available right now.

"Water drains from above and some water drains along the red line in the second photo. The window guy and handyman have mentioned that could an area with faulty flashing. "

What flashing,I don't see any faulty or otherwise? I'm accustomed to that trim board being at least 1" higher with step flashing visible. What do you think Millman ?

The roofer has said that the flashing is behind the wood and stucco. You can see a little metal in the corner which is part of the flashing sticking out.

I assume he reused the flashing that was there? Or did he pull off the wood to install new flashing behind it?

" The roofer has said that the flashing is behind the wood and stucco. "

" What flashing,I don't see any faulty or otherwise? "

" I assume he reused the flashing that was there? Or did he pull off the wood to install new flashing behind it? "

I see what could be flashing but I would have expected something a little more visible. I almost think he did as Hallett suspects as that wood does not appear to be recently and reinstalled removed to me.

No way he pulled that old wood. I wouldn't touch it unless it was in the contract and it was all being replaced on the roof to wall intersections. Even if he wove in with the old, depending on the roof before, the step might not be the right size any longer.

Couple that with the fact that the stucco just leaks and all those junctions with the stucco and the wood are all leakers as well.

There is clear evidence of rot in the wood adjacent to the window in the last picture. Roof needs gutters above that window or this will continue to happen. Any volute of water dumping off in in a concentrated fashion like that is going to create issues.

My roofer is still missing in action and a no show for his water test. I purchased a 16 ft rigit hose extension and did my own water test today. No leaking in any of the red marked areas below but when I spray the area marked in green in the second pictureI get water almost immediately coming through into the entry way. The third photo is the the window in the corner with the storm window removed. It does seem like the sill is cracked and rotted.

This whole area seems tied into tother and I wish that rotted wood had been replaced when the roof was redone. Will would it be difficult to replace wood and the sill of this window without disrupting the new roof?

Roofer is mostly right here then. Window trim needs to be re-done here.

And for the record, until you get gutters on that upper roof, this window will continue to rot prematurely.

What sort of gutters would you recommend for the upper roof? Similar to the ones below? Any way to make them look visually appealing?

Yup the windowsill is not the roofers responsibility. That needs repair asap

" Any way to make them look visually appealing? "

They are gutters, and looks are less important in the bigger picture than rotting wood and water damage. Use the 5" instead of 6" K style gutters,

Not sure how visually "unappealing" a bronze/brown K-style gutter would be here. Certainly less unappealing than a gushing leak and rotted trim.

"Yup the windowsill is not the roofers responsibility. That needs repair asap"

I'll work on getting the windowsill repaired. HALLETT, while the contract was for a roof replacement, the contractor is a window/siding/roofing company. 10 years ago he removed that window and had it rebuilt and replaced it and re-roofed and flashed that area. I called him again when I had the leak and agreed to replace the roof. Maybe I am naive, but if the roof replacement doesn't solve the issue, wouldn't one try to help the custumer after spending 65,000 on a roof replacement--particularly if one was a roofing/siding/window contractor? I felt like he just put on the expensive new roof and then largely walked away.

" but if the roof replacement doesn't solve the issue, wouldn't one try to help the custumer after spending 65,000 on a roof replacement--particularly if one was a roofing/siding/window contractor "

One would think so but in today's day and age, one never knows. Customer service in a lot of areas of the world went on vacation with common sense.

No overhang, no gutters and the window is sitting just above and just below roof valleys. Bad design.

Water is getting behind the storm, the storm has probably been trapping the water and the sill extension may not even be sloped and not able to drain.

I would look at moving the window to the left, eliminating it altogether or installing a porthole in its place.

If a 65K client can't get a stop by, that's not a great commentary on the contractor if that is exactly how it is playing out.

Progress is being made and I’ve found someone who seems willing to work to solve the problem. The valley was redone and he mention it was a mess of nails under the shingles. The leaking was drastically inproved but still had some leaking during heavy rain and seemed to coming from the area just right of the window will all that caulk. i replaced window and rhe wood next to it and the flashing was redone correctly behind it Gutters were installed on the upper roof and the left end of rhe lower gutter capped and additional punch out to allow more drainage if back up. ifnit doesnt work we’ll need to look at valley above as well but its been raining the past two days and its been dry inside. Will need to paint new window to match the storms but i think the window style fits. i saved the old window but so far i am happy

Gutters and flashing were your friends here. Thanks for the update.

Timing is everything. Maybe more artificial than intelligence.