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replace the seal and use plenty of adhesive. also sand the side of the seal you are putting the glue on lightly with 100 grit sandpaper. this removes the mold release agent that is on the new seal
 

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Make sure that the water in your trunk is coming from you rear window. My 68 has only seen rain 3x in last 14 years and all moisture after the rain came from the rear window.Check your package tray to make sure it is nice and dry.i hope so!
 

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Tail lights

I will have to agree, one of the things often over looked is the tail light gaskets.
The wifes car had a problem with the truck acting as a water storage device.
To my suprise when working on the tail light, the gaskets where missing or in such bad shape the gaskets did little to keep water out
 
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