backdrafting smoke at pipe connections

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I'm surprised you just nail through the shingles into the decking -- I've always worked diligently to not poke holes in my roof!
I drill a pilot hole, then use a heavy wood screw or even lag screw and put silicone or roofing caulking in the pilot hole plus on the head after. I'm with you, water seems to get in the smallest of cracks and at the worst of times. Keep in mind that all your shingles are just nailed in, so it's not that big a deal.
 
If you look at it a bit should be able to slip the mounting tab under a shingle edge still want to caulk lag bolt though. Use stainless bolts/ screws if possible.
 
image.jpg image.jpg I thought I would post a picture of the chimney and cap. I think it's only about 5 ft above the roof here. Do you think I'd need to anchor it if I put up another section? Also, the cap already looks like it would resist down-drafting. Do you agree, or am I missing something? As always, thanks to all of you for collective wisdom.
 
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