01 - Preheat oven to 350°F. Grease a 9x13-inch baking pan thoroughly with cooking spray or butter.
02 - In a large mixing bowl, combine yellow cake mix, eggs, crushed pineapple with juice, vegetable oil, and water. Beat with electric mixer on medium speed for 2 minutes until batter is smooth and well combined.
03 - Pour batter into prepared baking pan. Bake for 28-32 minutes until golden brown and a toothpick inserted into the center comes out clean.
04 - Let cake cool in pan for 10 minutes. Using the handle of a wooden spoon, poke holes evenly across the entire surface of the cake, spacing approximately 1 inch apart.
05 - In a medium bowl, whisk together sweetened condensed milk and coconut milk until completely smooth and combined.
06 - Slowly pour the milk mixture evenly over the warm cake, ensuring it seeps into the poke holes. Allow liquid to absorb completely, about 5 minutes.
07 - In a separate bowl, whisk together instant vanilla pudding mix, cold milk, and pineapple juice. Continue whisking for 2 minutes until pudding begins to thicken.
08 - Spread the thickened pudding evenly over the entire surface of the cake, creating a smooth layer.
09 - Cover pan with plastic wrap or foil. Refrigerate for at least 1 hour, or up to overnight, until completely chilled and set.
10 - Once fully chilled, spread thawed whipped topping evenly over the entire cake surface using an offset spatula.
11 - Sprinkle toasted coconut flakes generously over the top. Arrange fresh pineapple chunks and maraschino cherries decoratively across the surface. Slice into 12 equal portions and serve cold.