How to fill this gap between timbers?

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There is a 5mm gap between the bottom of a stringer and the skirting. What can I fill the gap with? Can I put some foam in and then easifill? Or is this a caulk job…
 

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Caulk always seems to crack or the paint peels off it, is there no better way?
Rip out the skirting and replace it with a piece that actually fits correctly. Anything else will potentially move, crack and show through over time.

BTW done properly the bottom of the stringer should have been terminated on a plumb cut, not just continue down like that.
 
use tubed cove adhesive from ts . same as caulk but doesn’t shrink and crack. and it’s cheaper.
 
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