Scoop the softened ice cream onto the baking sheet, distributing evenly. Use a large offset spatula to spread the ice cream in an even layer. Cover the ice cream with a second piece of parchment paper. Freeze for at least 6 hours, up to overnight. Place another baking sheet in the freezer to chill.
Fill a bowl large enough to fit the cookie cutter with hot water.
Remove the empty chilled baking sheet from the freezer and line with parchment paper.
Remove the ice cream from the freezer. Peel the top layer of the parchment paper off the ice cream. Working quickly, dip the cookie cutter in the hot water and press into the ice cream to cut out shapes. You may need to wiggle the cookie cutter around a little to get the shape to release. Use an offset spatula to transfer the shapes to the clean baking sheet. Return to the freezer.
Fill a medium bowl with very hot water.
Remove the ice cream pops from the freezer. Place a metal skewer into the hot water for 10 seconds. Working carefully and quickly, insert the skewer 3 inches (7 cm) into the base of a pineapple pop. Remove the skewer and immediately insert a popsicle stick into the space created by the skewer. Repeat with the remaining pops.
Return the pops to the freezer for 1 hour.
While the pops set, make the magic shell. In a wide and shallow microwave-safe dish, combine the white chocolate chips and coconut oil. Microwave in 30-second intervals, stirring between, until melted and smooth.
Continue stirring the magic shell until it cools down, about 3 minutes. Add the yellow food coloring, a few drops at a time, and stir until a pale, buttercup yellow color is achieved.
Remove the ice pops from the freezer. Pick up a pop by the stick and quickly dip the ice cream into the magic shell to coat completely. Sprinkle green sanding sugar over the top section of the pineapple to resemble the crown. Repeat with the remaining pops.
Return the pops to the freezer for 10 minutes to set and harden completely. Store in the freezer until ready to eat.