This recipe works with fresh pineapple, but save some time and effort and use a already packaged frozen pineapple if pineapple isn't on the shelves of your local market.
In a blender, pulse the cold pineapple until only tiny chunks remain. Spoon into a large bowl.
Fold the cool whip. Whisk the cream of coconut, rum, flaked coconut, and lime zest together in a small bowl. Fold into the pineapple mixture.
Divide the mixture evenly into popsicle molds and allow to freeze over night.
When ready to serve, make the chocolate coating. Toss the coconut oil and chocolate chips in a microwave safe bowl. Heat in 20 second bursts, stirring a bit inbetween, until chocolate is melted enough to stir smooth. Pour the chocolate coating into a tall glass, wide enough that the pops can fit in. Dip each pop, one at a time, allowing the coating to set about 5 seconds before sprinkling with extra coconut flakes if desired. Serve responsibly.