Pineapple Poke Cake

This refreshing pineapple poke cake transforms a simple boxed mix into a tropical delight that tastes like summer sunshine on a plate. Each slice reveals layers of moist vanilla cake infused with pineapple juice, creamy vanilla pudding that seeps into every nook, and a cloud-like whipped topping studded with juicy pineapple pieces. The clever addition of pineapple rings on the bottom creates a built-in decoration that adds both visual appeal and concentrated bursts of flavor. Perfect for warm-weather gatherings, this effortless dessert brings a taste of the tropics to any occasion without hours of baking.

I first made this cake for a neighborhood block party when I needed something that could feed a crowd without requiring hours in the kitchen. It disappeared faster than any other dessert on the table! My husband, who typically passes on cake in favor of cookies, asked me to make it again the following weekend for just our family. Since then, it's become my signature potluck contribution — I've even had friends text me before gatherings asking if I'm bringing 'that amazing pineapple cake.' Last summer, my mother-in-law requested the recipe after her third helping at our family reunion. When a dessert converts even the non-cake people, you know it's something special!

Ingredients You'll Need

• 1 box white or vanilla cake mix: The blank canvas for our pineapple creation; either flavor works beautifully
• 3 eggs: Or whatever the cake mix calls for; provides structure and richness
• ⅓ cup vegetable oil: Or whatever the cake mix calls for; adds moisture and tenderness
• 1 can (20 oz) pineapple rings in juice: Provides both decoration and the pineapple juice for the cake batter
• 1 can (8 oz) crushed pineapple, drained: Creates delicious pineapple-studded topping for maximum tropical flavor
• 2 packages (3.4 oz each) instant vanilla pudding mix: Creates the creamy filling that soaks into the cake
• 3 cups cold milk: Activates the pudding; make sure it's cold for proper setting
• 1 container (8 oz) whipped topping, thawed: Provides the light, fluffy layer on top; Cool Whip or homemade works
• Maraschino cherries (optional): For decorative garnish with a pop of color

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Step-by-Step Cooking Instructions

Prepare Your Space:

Begin by preheating your oven according to the cake mix directions, typically 350°F (175°C). Grease a 9×13-inch baking pan generously with cooking spray or butter. Having your workspace prepared before you start mixing ensures a smooth baking process.

Prepare the Pineapple:

Open the can of pineapple rings and drain the juice into a measuring cup – you'll need this for the cake batter. If the juice doesn't quite reach the amount of liquid called for on the cake mix box, add water to make up the difference. Pat the pineapple rings dry with paper towels to remove excess moisture, which helps them stay in place when you add the cake batter.

Arrange the Pineapple:

Place the pineapple rings in a single layer on the bottom of your prepared baking pan. You can arrange them in neat rows or slightly overlapping for complete coverage. If using maraschino cherries, place one in the center of each pineapple ring for a classic pineapple upside-down cake look. This bottom layer will become a decorative top when serving pieces directly from the pan.

Mix the Cake Batter:

In a large mixing bowl, combine the cake mix, eggs, oil, and the reserved pineapple juice (plus any additional water if needed) according to the package directions. Beat with an electric mixer on medium speed for about 2 minutes until the batter is smooth and well combined. The pineapple juice substitution is the secret to infusing pineapple flavor throughout the cake.

Bake the Cake:

Carefully pour the cake batter over the arranged pineapple rings, trying not to disturb their placement. Gently spread the batter to ensure even coverage all the way to the edges of the pan. Bake in the preheated oven according to the cake mix package directions, typically 25-30 minutes, until a toothpick inserted in the center comes out clean or with just a few moist crumbs.

Cool the Cake:

Remove the baked cake from the oven and place it on a wire cooling rack. Allow the cake to cool completely in the pan, which usually takes about 1-2 hours. The cake must be completely cool before moving on to the next step, or the heat will prevent the pudding from setting properly.

Create the Pudding Mixture:

While the cake is cooling, prepare the pudding by whisking together the instant vanilla pudding mix and cold milk in a medium bowl until well combined and starting to thicken, about 2 minutes. Place the bowl in the refrigerator to let the pudding thicken slightly while the cake finishes cooling, about 5-10 minutes. You want the pudding to be pourable but beginning to set.

Poke and Fill the Cake:

Once the cake has cooled completely, use the handle end of a wooden spoon to poke holes all over the cake's surface, spacing them about 1 inch apart. Make sure to poke all the way to the bottom of the cake but not through the pineapple layer. Pour the slightly thickened pudding mixture evenly over the cake, using a spatula to guide it into the holes. Gently tap the pan on the counter a few times to help the pudding settle into the holes.

Add the Topping:

Spread the thawed whipped topping evenly over the pudding layer with a spatula, creating a smooth, even surface. Open the can of crushed pineapple and drain it thoroughly – excess moisture will make the topping runny. Sprinkle the drained crushed pineapple evenly over the whipped topping layer.

Chill to Perfection:

Cover the cake with plastic wrap or the lid of your baking dish and refrigerate for at least 4 hours, but preferably overnight. This chilling time allows the pudding to fully set and the flavors to meld together. The cake actually improves after a day in the refrigerator, making it perfect for preparing ahead.

My first attempt at this cake taught me the importance of patience! I was in a hurry and poured the pudding over a still-warm cake, resulting in a soggy mess. Now I make sure to allow plenty of cooling time. I've also discovered that using pineapple juice instead of water in the cake mix makes a huge difference in the flavor – that subtle infusion of pineapple throughout the cake elevates the entire dessert. Another trick I've learned is to save a few pineapple rings to chop up and mix into the whipped topping for extra pineapple flavor and texture in every bite.

Flavor Variations

While the classic pineapple version is delicious, you can easily customize this versatile cake. For a piña colada twist, add 1 teaspoon of coconut extract to the cake batter and sprinkle 1/2 cup toasted coconut over the whipped topping along with the crushed pineapple. For a tropical medley, substitute a can of tropical fruit cocktail (drained) for the crushed pineapple topping. If you're lucky enough to find pineapple pudding mix, use it instead of vanilla for an intensified pineapple flavor throughout.

Make-Ahead & Storage Tips

This cake is the perfect make-ahead dessert. Prepare it up to 24 hours before serving and keep it refrigerated. The flavors actually develop and improve overnight as the pudding fully infuses the cake. Leftovers can be stored covered in the refrigerator for up to 3 days, though the whipped topping may begin to deflate slightly after that time. For longer storage, you can freeze individual portions for up to 6 weeks – simply thaw overnight in the refrigerator before enjoying.

Serving Suggestions

Serve this pineapple poke cake directly from the baking dish, cutting into squares to reveal the beautiful pineapple ring pattern on the bottom. For a more elegant presentation at dinner parties, consider making individual servings in clear trifle cups or dessert glasses, layering cubes of the prepared cake with extra pudding and whipped topping. A sprinkle of toasted coconut or a fresh mint leaf adds a sophisticated finishing touch.

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Perfect Occasion Pairings

This refreshing cake is ideal for spring and summer gatherings when lighter desserts are appreciated. It's perfect for potlucks, picnics, and backyard barbecues because it travels well and stays fresh in the refrigerator. The tropical flavors pair beautifully with grilled foods and summer cocktails. For a themed event, serve alongside other tropical desserts like coconut macaroons or key lime bars for a dessert table that transports guests to an island getaway.

I love serving this cake at outdoor summer gatherings when everyone is craving something cool and refreshing. There's something about the combination of moist cake, creamy pudding, and bright pineapple flavor that perfectly captures the essence of summer. What makes me smile most is watching guests' faces light up when they take that first bite – the surprise of discovering the pineapple rings on the bottom and the way the creamy pudding has transformed a simple cake into something special. It's the kind of dessert that creates a moment of pure joy around the table, and isn't that what sharing food is all about?

Frequently Asked Questions

→ Can I use fresh pineapple instead of canned?

Yes, but you'll need to create your own juice for the batter and slice the pineapple thinly. Canned is easier since it comes ready to use.

→ How long does this cake stay fresh?

When refrigerated in an airtight container, this cake stays fresh for up to 3-4 days. The texture is actually best on day 2.

→ Can I freeze this poke cake?

Yes, you can freeze it for up to 2 months. Thaw overnight in the refrigerator before serving for best results.

→ What other pudding flavors work well?

Coconut pudding works great for a piña colada flavor, or try banana pudding for a tropical twist.

→ Do I have to use Cool Whip?

No, you can substitute with 3 cups of homemade whipped cream (1.5 cups heavy cream whipped with 3 tablespoons sugar).