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My house has vinyl siding. If I want to hang something on an exterior wall, can I just attach it with screws drilled through the siding? Or do I need to do anything to prevent water from seeping in around the screws?

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The siding needs to remain free to expand and contract. So cutting at least a slot , then hanging something through that would work, but would be unsightly, and would leak water through the hole. So I think that finding some kind of gasket or trim piece (such as is found where your vents protrude through siding) and trimming with J-channel all around it would look better and would be less prone to leaks.

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When you say that the siding needs to remain free to expand and contract, do you mean that it's bad for the attached item to press the siding against the old siding that is inside it? –  Vebjorn Ljosa Jul 21 '10 at 19:36
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Yes, fixing one spot in place may make the siding buckle at another place when it gets warm in the sun. You could work around it by piercing a short piece, and having the adjacent pieces overlap (forming your expansion joint without a bunch of extra trim). –  Liudvikas Bukys Jul 22 '10 at 18:01
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You should probably seal it with some kind of silicone based caulk. If water seeps in behind the vinyl you'd be inviting mold and other damage. Whenever I've attached things or drilled through my siding I've always used DAP clear silicone caulk to seal around the hole.

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