I worked in construction for a while, where "Caulk the shit out of it." was an everyday thing. Caulk the shit out of the open drywall corner, caulk the shit out of the split in the trim board you just put up, caulk the shit out of the window that leaks...the door that leaks, the electric box on the wall that leaks...the deck that leaks. We must have caulked the shit of of so much stuff, it's a wonder there's any shit left to caulk. But I bet all the shit I caulked ended up leaking later on!
Well as I have learned in waterproofing, "caulk the shit out of it" is short for "trap the water inside so it can rot faster."

Decks and their flashings and the contiguous building materials must be flashed properly too; caulking is not a substitute for correctly flashing to the building and other components.

Instead of lapping the flashing down over the deck edge, the flashing was short, and the gap made up for with caulking.
The long and the short of it, caulking the shit out of something is not the answer, it's the problem.

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