Bay window flat roof drain leaking

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Hi all

Currently renovating our bedroom. We have a bay window which has leaked on and off. We thought we fixed the leak by painting some of that liquid roof stuff on and repointing the stone. But there's been heavy rain and I think the internal drain is failing now. I noticed the damp again while repairing the cornice as the filler wasn't drying. I've scraped the filler out and the wooden lathe is damp/wet. This area of damp lines up with the drain for the flat roof. So that's my thinking, the drain needs fixing/replacing? But I have no idea how to go about that! Any ideas?
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It then comes out the side anda plastic pipe that goes into a downpipe
 
You've coated the surface but not sealed this to the outlet pipe. This is a common thing and difficult to do and get right

Looks like you'll need to form a new [wider] outlet in the surface and properly join and seal this to the pipe within the roof.

Google " flat roof flange " or " flat roof outlet " for the principle.
 
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