Infuriating leak

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Hello. I apologise if this should be in a more appropriate thread. I had a look but couldn't find one. Tearing my hair out here about this leak which proceeds from roof into bedroom, down same column to kitchen on one side and dining room on the other. The roof was replaced two years ago and was seemingly a very good job however this leak has persisted. It's directly underneath where the flat roof meets the pitched. Definitely worse when it rains. Explained this to roofer who came back and ripped up the lower tiles. Couldn't see anything of note. Still persisted. He came back again and fibre-glassed further up the roof and over the joint into the gutter in case water was pooling and over-running somehow. I appreciate some of the photos may look like rising damp but I went under the floor in the dining room and there is no damp there. As I said it's all down this one column and definitely worse when it rains. It even appears to spread across the bedroom as shown in one picture. I'm reluctant to get the same roofer back as although trust him, he's had 2 or 3 looks at it and he's none the wiser as to how rain is getting in. If you can see that corner on the exterior picture the soffit/fascia is drooping and there's a random pipe sticking out in the corner which I assume is from an old water tank. Certainly not used now. All this is lower than the leak mark in the bedroom though so unless it's spreading upwards, can't be a cause? I'm just wracking my brains to consider anything that might be contributing to it. Any ideas would be very gratefully received? Ignore the white on the house. We're currently in the process of painting it. Many thanks

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I would try a flashing under the tile as it meets flat roof as possibly the rain is tracking under the tile that goes to the gutter also you have a gap under the soffit on the flat roof so gutter may be overflowing and water running down back side and throug the gap.
 
I would try a flashing under the tile as it meets flat roof as possibly the rain is tracking under the tile that goes to the gutter also you have a gap under the soffit on the flat roof so gutter may be overflowing and water running down back side and throug the gap.
Thanks. The roofer put fibreglass all the way across under the tile that meets the flat roof. I also thought the gutter might be overflowing but I've been up there in heavy rain and there's no obvious signs of any water getting in
 
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There isn't any signs of water there exterior or interior. It's a different room from where the leak appears
 
Could it be am issue higher up and the water is getting in and then tracking down membrane and cannot escape out where the flat roof meets. Is the wet area inside with the flue for example ? Also what's the random rust streak about
 
Could it be am issue higher up and the water is getting in and then tracking down membrane and cannot escape out where the flat roof meets. Is the wet area inside with the flue for example ? Also what's the random rust streak about
That's a good shout. Wouldn't there be some signs inside the loft then? Drips off membrane or at least signs of moisture? There no real signs of wet around the flue inside but maybe just after it towards join with the flat roof. The problem is it's so hard to get in to have a look inside. I've been up there both inside and out when it's been pouring down hoping to see/hear some water movement but nothing. The signs of leakage were there before we had the roof replaced but having a new roof or at least extending the fibreglass appears to have made it worse.
The rust streak I assume just came from a bad nail and I've never given it much thought.
Thanks
 
Thanks. The roofer put fibreglass all the way across under the tile that meets the flat roof. I also thought the gutter might be overflowing but I've been up there in heavy rain and there's no obvious signs of any water getting in
Is there a short/eaves course, beneath the slates where the flat roof meets the pitched roof?
 

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