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pineapple upside-down cake

Golden, caramelized pineapple slices on top of a freshly baked pineapple upside-down cake.
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Pineapple Upside-Down Cake is a classic dessert featuring a moist cake topped with caramelized pineapple rings and maraschino cherries. This vintage favorite is simple to make, yet it’s full of flavor, with the sweetness of the pineapple and the rich, buttery caramel creating a perfect balance. A showstopper at any gathering!

Ingredients

Scale

For the Topping:

1/4 cup unsalted butter (melted)

1/2 cup brown sugar (packed)

8–10 pineapple rings (canned or fresh)

8–10 maraschino cherries (or fresh cherries if preferred)

For the Cake:

1 1/2 cups all-purpose flour

1 cup granulated sugar

1/2 cup unsalted butter (softened)

2 large eggs

1 teaspoon vanilla extract

1/2 cup milk

1 1/2 teaspoons baking powder

1/4 teaspoon salt

1/4 teaspoon ground cinnamon (optional, for extra flavor)

Instructions

Prepare the Topping:

Preheat your oven to 350°F (175°C). Grease a 9-inch round cake pan with butter or cooking spray.

In a small bowl, mix together the melted butter and brown sugar. Pour this mixture evenly into the bottom of the prepared cake pan.

Arrange the pineapple rings over the brown sugar mixture, placing one in the center and others around the edges. Place a maraschino cherry in the center of each pineapple ring.

Make the Cake Batter:

In a separate large mixing bowl, cream together the softened butter and granulated sugar until light and fluffy (about 3 minutes).

Add in the eggs, one at a time, beating well after each addition. Stir in the vanilla extract.

In another bowl, whisk together the flour, baking powder, salt, and cinnamon (if using).

Gradually add the dry ingredients to the wet ingredients, alternating with the milk. Begin and end with the dry ingredients, mixing just until combined. Be careful not to overmix.

Assemble the Cake:

Pour the cake batter evenly over the pineapple and caramel mixture in the cake pan, smoothing the top with a spatula.

Tap the cake pan gently on the counter to remove any air bubbles.

Bake the Cake:

Bake in the preheated oven for 35-40 minutes, or until a toothpick inserted into the center of the cake comes out clean.

If the top begins to brown too quickly, cover it loosely with foil during the last 10 minutes of baking.

Cool and Serve:

Let the cake cool in the pan for about 10 minutes. Then, carefully invert the cake onto a serving plate. The pineapple topping should now be on top.

Serve warm or at room temperature, and enjoy!

Notes

For a lighter version: Use a sugar substitute for the brown sugar and granulated sugar, and opt for a reduced-fat butter.

Pineapple Options: You can use fresh pineapple if desired, but canned pineapple rings work best for the classic look. Ensure the pineapple is well-drained to prevent excess moisture in the cake.

Topping Variations: You can also try adding chopped pecans or walnuts on top of the pineapple rings for added texture and flavor.

Make Ahead: This cake can be made ahead of time and stored in an airtight container for up to 3 days. To reheat, simply warm it up in the oven at 300°F (150°C) for about 10 minutes.

Nutrition

Keywords: pineapple upside-down cake

Find it online: https://mirayamsrecipe.com/pineapple-upside-down-cake/