Preheat the oven to 350°F. Lightly coat a 9x13-inch baking dish with nonstick cooking spray.
Arrange 2 (8-ounce) cans drained pineapple slices in a single layer on the bottom of the prepared baking dish.
Prepare 1 box yellow cake mix according to the package directions. Pour the batter evenly over the pineapple slices.
Bake according to the cake mix package directions, or until a toothpick inserted into the center comes out clean.
Allow the cake to cool completely in the baking dish.
Using the handle of a wooden spoon, poke 12 to 16 holes evenly across the cooled cake.
In a medium bowl, whisk together 1 (3.4-ounce) box instant vanilla pudding mix and 1½ cups milk until smooth and slightly thickened.
Pour the pudding mixture evenly over the cake, using a spatula to gently spread it across the surface and into the holes.
Refrigerate the cake for 1 hour to allow the pudding to set.
Spread 1 (8-ounce) tub whipped topping evenly over the chilled cake.
Sprinkle 1 (8-ounce) can drained pineapple chunks over the whipped topping.
Refrigerate for at least 2 more hours before serving. For the best flavor and texture, prepare the cake a day in advance and keep it refrigerated until ready to serve.