chimney leaks

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Daddytron

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Every time it rains with a slight wind, I can hear rain tinging inside my chimney. I took off the clean-out cover and maybe an ounce of water came out of it. After inspecting it, the rain is leaking from the upper pipe in the picture and dripping around the smaller pipe that the furnace and hot water tank vent into. Is there any way to prevent this, and is there anywhere I should be looking for water damage?

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There is probably a rain collar around the pipe above roof level. These need to be caulked periodically. Do not use silicone to caulk this and if you are not comfortable on the roof, hire someone.
 

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