Preheat the oven to 350°F (175°C). Lightly grease a standard muffin pan with baking spray and set it aside. In a food processor, add the flour, sugar, and salt, then pulse a few times to combine the dry ingredients. Add the chilled butter cubes and pulse again until the mixture resembles coarse crumbs. If the dough appears too dry and sandy, add one tablespoon of ice water and pulse. If needed, add a second tablespoon and pulse just until the dough comes together. Roll the dough into 1½-inch balls and press each one into the prepared muffin pan, shaping them into cups. Bake for 16 to 18 minutes, or until the edges are lightly golden. The dough will puff slightly during baking, so once out of the oven, use the back of a spoon to gently press down the centers again while still warm to redefine the cup shape. Allow them to cool in the pan for 5–10 minutes before transferring to a wire rack to cool completely.

In a medium bowl, whisk together the instant vanilla pudding mix and coconut milk until the mixture thickens. If desired, fold in ½ cup of toasted shredded coconut for added texture. For a smooth and silky filling, skip the shredded coconut and instead sprinkle the toasted coconut generously on top of the whipped cream later. This keeps the filling smooth while preserving the crunch of the toasted coconut topping, especially when using coconut flakes.

Fill each cooled cookie cup with a spoonful of the coconut cream filling. Top with a swirl of whipped cream and finish with a sprinkle of toasted coconut. Chill the assembled cookie cups in the refrigerator for at least 30 minutes to allow the filling to set before serving.