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I have been installing new clapboard siding on my house. It is primed finger jointed cedar. The one time I had a friend help me he questioned my method of caulking. What I have been doing is installing the lengths then applying a bead of caulk to the ends where they meet the trim boards (I think that's what they are called. Basically, these are the long boards that run from the top to bottom of each corner) then finger smoothing the bead.

He suggested that I should be applying a thick bead of caulk, then apply the board squashing the board into the caulk.

Is there a preferred method? And is it one of the ones I listed?

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I don't think your friend's suggestion is bad, but I'd still want to be sure the caulk extended all the way to the exposed surface of the siding. Better not to let water get into the crack at all than to let it get in and stuck between siding and trim but blocked from penetrating further by caulk.

Why?

Because in winter, water that's in the crack will freeze, expand, and make bigger cracks. Water on the surface can do no harm.

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