Description

Pineapple Upside Down Cake is a retro classic featuring caramelized pineapple slices and maraschino cherries atop a moist, ultra-tender vanilla cake. This recipe uses canned pineapple in juice to ensure the cake remains juicy and flavorful, with pineapple juice incorporated into the batter for added tropical essence. The cake is baked to golden perfection, with a sticky, caramelized topping that beautifully contrasts the soft crumb inside.

Ingredients

Scale

Topping

565g/20 oz canned pineapple slices in juice (not in syrup)
12-18+ maraschino cherries
60g/4 tbsp unsalted butter, melted
1/2 cup brown sugar

Cake Batter

1 1/2 cups flour
1 tsp baking powder
1/4 tsp baking soda (or substitute 1 tsp baking powder)
1/4 tsp salt
1/3 cup milk (full or low-fat)
1/4 cup pineapple juice (reserved from canned pineapple)
1/4 cup sour cream (full fat, or substitute plain yogurt)
1 tsp vanilla extract or essence
115g/1 stick unsalted butter, softened to 18°C/64°F
3/4 cup white sugar
2 large eggs, at room temperature
Any leftover pineapple, chopped

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Instructions

Preheat Oven: Set your oven to 180°C/350°F (160°C fan) to warm up while preparing the cake.
Prepare Topping: In a baking pan, combine the melted butter and brown sugar evenly across the bottom. Arrange pineapple slices over the sugar mixture, then place maraschino cherries in the centers of pineapple rings or between slices. This will create a sticky caramelized topping once baked.
Mix Dry Ingredients: In a separate bowl, sift together the flour, baking powder, baking soda, and salt to ensure even leavening.
Combine Wet Ingredients: In another bowl, whisk together the milk, pineapple juice, sour cream, and vanilla extract until smooth and well blended.
Cream Butter and Sugar: Using a mixer, beat the softened butter and white sugar until light and fluffy, which adds air to the batter for a tender crumb.
Add Eggs: Beat in the eggs one at a time, ensuring each is fully incorporated before adding the next to maintain emulsion and texture.
Incorporate Dry and Wet Ingredients: Alternately add the dry ingredient mixture and wet ingredient mixture to the creamed butter and sugar, starting and ending with dry ingredients. Mix gently to combine without overmixing.
Add Pineapple Chunks: Fold in any leftover chopped pineapple for extra moisture and bursts of fruit within the cake.
Assemble Cake: Pour the batter evenly over the arranged pineapple and cherry topping in the pan, smoothing the surface.
Bake: Place the pan in the preheated oven and bake for approximately 45 minutes, or until a toothpick inserted into the center comes out clean.
Cool and Flip: Allow the cake to cool in the pan for about 10 minutes. Then carefully invert the cake onto a serving plate so the pineapple and cherries are on top, revealing the beautiful caramelized topping.

Notes

Use canned pineapple in juice, not syrup, to avoid excessive sweetness and maintain moisture.
The number of maraschino cherries can be adjusted based on preference; more cherries add extra sweetness and decoration.
Softened butter should be at around 18°C/64°F for proper creaming consistency.
Ensure eggs are at room temperature to help them incorporate smoothly into the batter.
Some pineapple juice from the can is reserved to add flavor and moisture to the batter, so don’t discard it.
The cake can be served warm or at room temperature and pairs well with whipped cream or vanilla ice cream.

Nutrition

Serving Size: 1 serving
Calories: 319 kcal
Sugar: 34 g
Sodium: 162 mg
Fat: 14 g
Saturated Fat: 8 g
Unsaturated Fat: 5 g
Trans Fat: 1 g
Carbohydrates: 47 g
Fiber: 1 g
Protein: 3 g
Cholesterol: 61 mg