• Preheat the oven to 350 degrees F.
• Spray a 9×13-inch pan with non-stick cooking spray and set aside.

MAKE THE CAKE:

• Drain the pineapple well and reserve the juice.
• In a large bowl, combine cake mix, water, vegetable oil, and eggs. Mix until thoroughly combined. Add ⅔ cup of crushed, drained pineapple.
• Pour batter into the prepared baking pan smooth into an even layer.
• Bake for 30 minutes or until a toothpick inserted in the center comes out clean.
• Cool the cake completely, for about 1 hour.

POKE AND FILL CAKE:

• Use the handle of a wooden spoon to poke holes over each inch of the cake. Make about 80 holes (8 across by 10 rows). Set aside.
• In a medium bowl, combine the pudding mix, milk, vanilla, and ⅔ cup pineapple juice. Whisk together until smooth.
• Pour pudding over cake and spread evenly with a spatula, allowing the pudding to run into the holes in the cake.
• Cover and refrigerate the cake for 1 hour.

MAKE THE WHIPPED CREAM TOPPING:

• Pour the cold heavy whipping cream into the cold bowl and whip on high speed until medium to stiff peaks form, about 1 minute. Make sure it is thick.
• Add the remaining crushed, drained pineapple and powdered sugar. Whip together for about 20-30 seconds, and spread evenly over the chilled cake.
• Refrigerate cake for 3 hours before serving.