Add bananas, coconut cream, 1/4 cup toasted coconut flakes, frozen pineapple chunks, agave, and coconut extract to the bowl of a blender. Pulse until smooth.
Add 1 teaspoon toasted coconut flakes to the bottom of each popsicle mold. Top with 2 teaspoons of the drained crushed pineapple. Divide the banana mixture between the molds.