Roof leak below loft conversion

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I have a persistent roof leak into my son’s bedroom below our loft conversion. I have had a seemingly reputable roofer come twice to try and fix it but he’s run out of ideas and left me £325 poorer! He replaced some lead flashing under the gutter and also said the felt under the tiles is fine. It’s a weird leak in that it doesn’t leak every time it rains, only sometimes, almost like either there is a build up of water or only when the wind is blowing a certain way. When the water comes in though it’s quite heavy, ie literally running down the walls. Any thoughts / ideas / help please? I have attached various photos. Much appreciated.
 

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That lead work under the downpipe looks really inadequate to me. Badly done. And the lead work along those tiles. Any driving rain would easily get in under all that.
 
Thanks for your quick response much appreciated. We have lived here 12 years with no changes to the roof in that time and it’s only in the past year we have noticed the problems. Could that be lead related? Obviously don’t want to spend money unnecessarily. Thx.
 
Could the down pipe from the higher roof be overwhelming the gutter?
 
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Thanks for your reply. We’ve lived at the property many years and the problem has only recently started so I wouldn’t imagine it would be that.
 
It would be worth you standing outside during a heavy rainfall and watching how the roof and gutter perform, you may get wet but it may tell you what is causing it too.
 
We’ve lived at the property many years and the problem has only recently started so I wouldn’t imagine it would be that.
How long something lasts and how well it performs depends on how well it was built and how well it was designed in the first place!
My general impression of loft conversion company's is you have had 5yrs more than most before problems arise.
 
Extend the rainwater pipe from the main roof into the gutter below and see if that helps.
 
Extend the rainwater pipe from the main roof into the gutter below and see if that helps.
I can't see that being the issue as the OP says it only happens now and then. The side cheek of the dormer where the ridge tiles are look like a bodge to me, that's where I would start looking because it will be sheltered at times depending on wind direction.
 
Any chance water is getting in and down behind the tiles cladding the dormer?
 

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