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Then again, I'm one of those people that think a 70 pound chair in the back of a pickup at 70 miles per hour can indeed levitate and needs to be tied down.

Blue Runner hinted at something to check......there are drain holes in the tracks that can get clogged over the years and cause water to go the wrong way....check them.
Mine leaks when on the trailer with the bow raised, but not when sitting level in the water.....so when I have mine sitting on the trailer, but uncovered, I dont jack up the bow very high, just enough to keep water flowing out of the cockpit if it rains.
Heres a couple pics of the drain you are looking for.
From inside:
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From outside:
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I agree, if you want to keep whats in the boat going down the road, tie it down