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Advice on re-sealing exterior door frame to vertical wood siding

Can I get your thoughts on re-applying caulking between my exterior front door frame and wood siding? I noticed it's starting to deteriorate on the sides and I have to main questions:

  1. What type of caulk should I use? I'm planning on painting it to match the wood siding. It looks like my options are polyurethane or latex based, and I'm leaning more on polyurethane as it appears to be more durable of the two. Silicone doesn't seem applicable because paint won't easily adhere to it.
  2. Should I apply to the top of the door frame as well? It wasn't done originally but it seems to me that water can ingress and I'm not sure where it's going.

Photos:

Right side:

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Front:

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Left side:
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Right upper corner:
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Top:
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Left upper corner:
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Bottom corner:

enter image description here

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  • For most re-caulking jobs, you want to remove and clean the surfaces first.
    – crip659
    Commented Oct 19 at 16:37
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    I think @crip659 means "to remove the old caulk" etc. As to what to use, I've had good luck with OSI Quad Max—a poly sealant.
    – Huesmann
    Commented Oct 20 at 12:20
  • Thanks, I should have specified I'd scrape off the old caulk before re-applying. Should I also do the top of the door frame?
    – boat14
    Commented Oct 21 at 3:11

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