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Before I hire a roofing inspector to challenge what I consider neglect by my HOA, I wonder if how this drain is installed is acceptable and what type of material is this.? I've had leaking in my 8' window that is located below the side drains on the edge of the roof and even had a new window put in. The HOA keeps saying it's the window. When the HVAC installer was on the roof several weeks ago he took these pictures for me. I also discovered that the side drains above my window have been clogged -see pic of water against the side drain after 0.5" of rain two days before pic. The HOA has now snaked out the side drains. I know that only an opinion can be provided based on limited information, but with all the videos I have looked at this does not look right. No one did a job like this that I saw. Thanks!

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With any roofing membrane we are required to have fixation at all perimeter and curbs, that being said you have none of that and they seem to of bathtubed there material (field membrane running up and over the parapet or up a wall). The membrane has probably barely or has no glue to hold the membrane onto the parapet. Your scupper should be have a flang not a pipe that you cannot make watertight unless you put a sleeve inside and waterproof to your stripping. Your drain is wrong your pipe wrap is wrong i can only imagine what else is wrong. You need a new roof.
 

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If you don't know the material and how to get rid of an existing leak, you can hire a drain camera inspection. I think a professional who comes to your home will be able to tell you the principles of how this drain works. I also think a professional will be able to change a few positions of this drain, which will get rid of the leaks. Maybe the pipe has a hole due to corrosion causing the runoff. I'm not sure that this is the case. And I don't claim to be a professional or a roofer. I'm just sharing my thoughts on the topic. While you're waiting for the professional inspector to arrive, you can try to fix the leak where you can see it from the outside if you're too worried about it.
 
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