The rubber membrane was never attached to the drain flashing in this image
When a drain is leaking, it is not always necessary that which causes the leak. Because the drain is normally lower than the rest of the roof, a leak could start somewhere else and flow towards the drain underneath the roof membrane.
Ho to locate a leak around a drain:
Try to open the ceiling where the drain is coming through the roof and make a visual inspection
Clean all debris that has accumulated around the drain and strainer
Remove the strainer to make a visual inspection of the drain pipe from above
Make a close-up inspection of the roofing membrane and the drain flange to see if it hasn’t separated
If you can’t find an obvious problem, call an experienced roofing technician to find and repair the leak
Roof Drains that are clogged will cause leaks
Debris Around Flat Roof Drain Strainer
Watch the 3D video explaining how a roof drain should really work
How to inspect a roof drain for leaks
Remove the strainer
Check if debris has collected inside the drainpipe blocking it
Inspect the membrane that is attached to the drain to see if there are any tears or cracks
Remove all debris
Remove all water completely to make a visual inspection
Make sure to keep drains clean from debris once a week
Clean entire roof regularly to prevent debris flowing to drain during a rainstorm
Make sure drain pipes are unrestricted all the way
Replace broken plastic strainers with metal ones
If water is ponding around the drain area due to being too high, have a roofing contractor lower the drain
This is a 3 D Video explaining the proper configuration of a drain
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