Caulking skirting, before or after glossing?

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When caulking along the top of newly fitted skirting, do you caulk before glossing or afterwards, and why?.
 
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Recently did this and caulked first. Don't have a specific reason as to why, just chose to do it that way and it has turned out fine :)
 
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Caulking should not go on bare timber but after the first initial primer. It wont stick to raw timber and needs a coat of paint to make it adhere. Then all subsequent coats will cover the caulking.
 

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