Pineapple Delight Poke Cake

If there is one dessert that tastes like summertime in every bite, it's this Pineapple Delight Poke Cake. Light, creamy, and bursting with sweet pineapple flavor, this easy make-ahead dessert has become one of my favorite Bugsy and Company summer treats. Whether you're headed to a backyard barbecue, family reunion, church potluck, or just looking for something refreshing after dinner, this cake is always one of the first desserts to disappear.

Using a boxed pineapple cake mix keeps this recipe incredibly simple, while one easy swap takes the flavor to the next level. Instead of using water, the cake is made with pineapple juice from a can of crushed pineapple, giving every bite even more tropical flavor. Once the cake is baked, it's soaked with sweetened condensed milk while still warm, creating an incredibly moist and tender cake that melts in your mouth.

The topping is what really makes this dessert special. A creamy vanilla or coconut pudding is mixed with whipped cream and sweet crushed pineapple before being spread over the cake. It's light, fluffy, and perfectly balanced with the rich, moist cake underneath. Finish it with the remaining Cool Whip, and you have a beautiful dessert that's as delicious as it is easy to make.

The hardest part about this recipe is waiting for it to chill! Giving the cake plenty of time to set in the refrigerator allows all of the flavors to come together, making every slice even better than the last.

Ingredients

Cake

  • 1 box pineapple cake mix

  • Ingredients listed on the cake mix box, except substitute 1 cup drained pineapple juice (from one 20 ounce can crushed pineapple) in place of the water

Filling

  • 1 (14 ounce) can sweetened condensed milk

Topping

  • 1 (5.1 ounce) package instant vanilla pudding mix or coconut cream instant pudding mix

  • 2 cups whole milk

  • 1 cup heavy whipping cream

  • 1 teaspoon vanilla extract

  • 1 (20 ounce) can crushed pineapple, well drained (reserve the juice for the cake)

  • 1 (8 ounce) container Cool Whip, thawed

Directions

  1. Prepare the pineapple cake according to the package directions, replacing the water with 1 cup of the drained pineapple juice from the can of crushed pineapple. Bake according to the package directions.

  2. Allow the cake to cool for about 10 to 15 minutes.

  3. While the cake is still warm, use the handle of a wooden spoon to poke holes all over the cake.

  4. Slowly pour the sweetened condensed milk evenly over the warm cake, allowing it to soak down into the holes.

  5. In a large mixing bowl, combine the instant pudding mix, whole milk, heavy whipping cream, and vanilla extract. Beat with a hand mixer for 2 to 3 minutes, or until the mixture begins to thicken.

  6. Fold the well-drained crushed pineapple and 1/2 cup of the Cool Whip into the pudding mixture until evenly combined.

  7. Spread the pineapple pudding mixture evenly over the cake.

  8. Top with the remaining Cool Whip, spreading it into an even layer.

  9. Cover and refrigerate for at least 6 hours, but overnight is even better.

  10. Slice and serve cold.

Bugsy Tips

  • Be sure to drain the crushed pineapple well so the topping stays thick and creamy.

  • Coconut cream pudding gives the cake a tropical twist, while vanilla pudding creates a classic pineapple dessert that everyone loves.

  • This cake is even better the next day after the flavors have had plenty of time to come together.

  • Garnish with toasted coconut, maraschino cherries, or a sprinkle of chopped pecans for an extra special presentation.

  • Store leftovers covered in the refrigerator for up to 4 days.

This Pineapple Delight Poke Cake is everything you want in a summer dessert. Cool, creamy, fruity, and incredibly easy to make. The moist pineapple cake, rich sweetened condensed milk, fluffy pineapple pudding, and Cool Whip topping come together to create a dessert that's perfect for every summer gathering. One bite, and you'll see why it's one of my favorite Bugsy and Company desserts!

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