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I'm putting some wainscoting in a kitchen this week and have been using caulking in some areas and spackling in others to finish it up. The caulking looks fine around the baseboard and the chair rail, but had to cut around a few windows, and though I didn't do a bad job, I'm no finish carpenter and needed a little extra help. I don't like the way the caulking leaves streaks on the wainscoting eventhough it's a small bead and tough to see. But on the other hand, sanding the spackling also seems to reveal the patch a bit. Just wondeirng how other people do it.
 

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what kind of caulking are you using?? If it's a really big gap put some wood filler or lightweight spackle... Caulking isn't made for big gaps that are bigger then 1/4 inch but you can always use a foam backer rod then caulk over..Bondo can also be used for big gaps, but it is a little hard to use if you have never used before...If you plain on painting the wainscotting spot prime all areas that have been caulked or filled otherwise you probally get some flashing...
 
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