Best Pineapple Upside Down Cake

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A delightful retro dessert featuring caramelized pineapple and cherries atop a moist, buttery cake.

Prep Time20

Cook Time50

Total Time1 10

Course: Dessert

Cuisine: American

Keyword: Comfort Food, Easy

Servings: servings

Calories: 350kcal

Preheat the oven to 350°F (175°C).
In a saucepan, melt 1/2 cup butter over medium heat. Stir in 1 1/4 cups dark brown sugar until dissolved and bubbly.
Pour this caramel mixture evenly into the bottom of a 9x13-inch baking dish.
Arrange the drained pineapple slices on top of the caramel. Place maraschino cherries in the center of each pineapple ring and anywhere else they fit for extra color and sweetness.
In a medium bowl, whisk together the flour, baking powder, and salt.
In a large bowl, cream together 1/2 cup softened butter, 1/2 cup granulated sugar, and 1/3 cup dark brown sugar until light and fluffy—about 2 minutes.
Add the eggs one at a time, beating well after each addition. Pour in the milk, 1/2 cup reserved pineapple juice, and almond extract. Mix until combined.
Gradually add the dry ingredients to the wet mixture, mixing just until smooth and no dry streaks remain.
Carefully spread the batter over the pineapple and cherries in the pan, smoothing the top with a spatula.
Bake for 45-50 minutes, or until a toothpick inserted into the center comes out clean and the top is golden brown.
Cool in the pan for just 5-10 minutes. Run a knife around the edges if needed, then invert the cake onto a large serving platter while it’s still warm.
Serve slices while the caramel is gloriously gooey.

For serving, pair with vanilla ice cream or whipped cream. Store leftovers tightly covered at room temperature for up to 24 hours.