Drain the crushed pineapple in a fine mesh strainer and reserve the juice. Let it sit to remove excess moisture.

Preheat your oven to 350°F (175°C) and grease a 9x13-inch baking pan.

Prepare the yellow cake mix according to package instructions using the reserved pineapple juice instead of water. Pour the batter into the prepared pan and bake for approximately 30 minutes.

Once baked, remove from the oven and allow it to cool in the pan for about 10 minutes. Then transfer to a wire rack to cool completely.

Poke holes all over the cooled cake using a skewer or fork, allowing the reserved pineapple juice to seep into the cake.

Spread the drained pineapple evenly over the top of the cake, filling in the holes.

In a large mixing bowl, whip the cold whipping cream and sugar until medium-stiff peaks form.

In another bowl, beat the softened cream cheese until smooth. Gradually mix in the cold milk until well combined.

Add the instant vanilla pudding mix to the cream cheese mixture and beat for an additional 2 minutes.

Gently fold the whipped cream into the cream cheese mixture.

Spread the creamy frosting evenly over the pineapple layer on the cake.

Cover the cake with plastic wrap or foil and refrigerate for at least 1 hour before serving.