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I'm referring to the trim board under the soffit. Should I caulk it to the wall? What about to the soffit? It has never been caulked before (house is over 40 years old). The overhang protects it and water shouldn't go up behind the board. I guess it would just be for aesthetic reasons to caulk it. I guess it could block small bugs if caulked. What are your thoughts on it?

 

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It will look some much crisper after you paint........if you caulk it. It is a rather large opening so the caulk may eventually crack........use an elastomeric caulk with lots of flex and you should be good to go. I use MaxFlex from Sherwin Williams.
 
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