Upside down or right side up, this delicious retro cake is perfect for all occasions!

Whenever I travel down to the South, I love indulging in a slice (or two) of dump cake. If you’ve never had it, it’s just as it sounds—dump a bunch of ingredients into a sheet pan, mix, and bake. It’s easy to make and incredibly delicious to eat. Another type of Southern cake that I can’t get enough of when I’m in the area is pineapple upside-down cake.
Known for its inverted and eye-catching design, it has historical roots as a “skillet cake,” made during times when food was cooked over a fire in skillets due to the absence of conventional ovens. The open flames would cook the cake thoroughly, and keeping the fruit on the bottom would allow it to get slightly caramelized but not burnt, as it was protected by the cake batter on top.
While pineapple upside-down cake is now usually prepared in an oven, it can be prepared in various types of pans beyond a skillet. This recipe calls for a Bundt cake pan, which creates an especially festive-looking cake with a lovely wreath shape. In addition to being a feast for the eyes, it’s beyond delicious and sure to be a standout dessert whenever you serve it.

Tips to make the perfect pineapple upside-down cake
Decorative and delicious, there are a few hacks you can follow to ensure your pineapple upside-down cake turns out picture perfect. For starters, don’t forget to grease your Bundt cake pan generously with butter and dust it lightly with flour (as instructed in the recipe) to prevent the cake from sticking to the pan when it’s time to flip it. Next, limit the number of pineapple rings to no more than eight slices to keep the cake from separating.
Unlike a dump cake or traditional yellow cake, this cake requires a delicate hand when preparing it—namely, when pouring the batter over the arranged fruit, it’s important to go slowly and gently to avoid disturbing the fruit pattern you painstakingly created. And of course, like any cake, make sure you let the cake cool after baking before trying to remove it from the pan, using a butter knife or spatula to gently loosen the edges.

How do I store leftovers?
Once the cake has cooled completely, any leftovers can be stored in an airtight container in the fridge for up to 5 days. For longer storage, you can freeze it either whole or sliced by wrapping it in a layer of plastic wrap followed by a layer of tinfoil or by placing it in an airtight container. The cake can be frozen for up to 3 months without compromising the taste, although the texture may change slightly the longer it is kept. Simply thaw it overnight in the refrigerator, and allow it to come to room temperature before serving.

Serving suggestions
The beauty of this cake is that it requires no extra accoutrements before serving. The glazed fruit serves as the icing and decoration, which also makes the cake taste delicious. However, it is even more delicious when served à la mode, warm from the oven with a scoop of Coconut Milk Ice Cream or Cottage Cheese Ice Cream. You could also serve it alongside this Coconut Tapioca dessert for an island-themed hangout with your friends. Serve these crispy Air-Fryer Pineapple Rings on the side and a batch of Classic Mai Tais to really liven up the party.


Pineapple Upside-Down Bundt Cake
Ingredients
- 5 tablespoons unsalted butter 1 tbsp softened for greasing pan; 4 tbsp melted for topping
- Flour for dusting pan
- 1 cup packed light brown sugar
- 8 pineapple rings (from a 20-ounce can) drained; reserve the juice
- 8 maraschino cherries pitted
- 1 box yellow cake mix (15.25 ounces)
- 4 large eggs at room temperature
- 1 box instant vanilla pudding (3.4 ounces)
- 1/2 cup whole milk
- 1/2 cup pineapple juice use reserved juice and add water if needed
- 1/2 cup vegetable oil
- 1 teaspoon vanilla extract optional
Instructions
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Preheat the oven to 325°F. Grease a 10-inch bundt pan with 1 tablespoon of softened butter, and then dust it lightly with flour to help release the cake later.
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Drizzle 4 tablespoons of melted butter into the bottom of the prepared pan. Evenly sprinkle the brown sugar over the butter. Arrange the pineapple rings on top, and place a maraschino cherry in the center of each ring.
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In a large bowl, combine the yellow cake mix, eggs, pudding mix, whole milk, pineapple juice, vegetable oil, and vanilla extract. Mix until just combined without overmixing.
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Slowly pour the batter over the pineapple topping in the bundt pan, ensuring an even layer. Bake for about 40-45 minutes or until a toothpick inserted into the center comes out clean.
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Allow the cake to cool in the pan for 10 minutes. Then carefully invert onto a serving plate, letting the extra topping drip over the cake. Serve warm or at room temperature.
Nutrition
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