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Pineapple Upside Down Cak

A nostalgic dessert that blends golden caramelized fruit with tender vanilla cake. This retro favorite features juicy pineapple slices and bright maraschino cherries on top, a soft and moist crumb flavored with pineapple juice throughout, and bursts of fruit folded within. It’s as visually stunning as it is delicious.
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Course: cake
Cuisine: Western
Keyword: pineapple upside down cake
Prep Time: 20 minutes
Cook Time: 45 minutes
Cooling Time: 20 minutes
Total Time: 1 hour 25 minutes
Servings: 10

Ingredients

For the Topping:

  • 60 grams approximately 4 tablespoons of unsalted butter, liquefied
  • Half a cup of packed brown sugar
  • One 565-gram 20 oz can of pineapple rings in natural juice (not syrup)
  • 12 to 18 maraschino cherries drained and dried

For the Cake:

  • One and a half cups of plain all-purpose flour
  • 1/4 teaspoon of baking soda alternatively, use a full teaspoon of baking powder
  • A quarter cup of sour cream preferably full fat (or substitute with plain yogurt)
  • Two large eggs brought to room temperature
  • One stick about 115 grams of unsalted butter, softened to approximately 18°C (64°F)
  • 3/4 cup granulated white sugar
  • 1 teaspoon of vanilla extract or essence
  • 1/4 cup of pineapple juice reserved from the canned fruit
  • 1/3 cup of milk either whole or low-fat
  • 1 teaspoon of baking powder
  • 1/4 teaspoon of fine salt
  • Any remaining pineapple slices finely chopped

Instructions

  • Preheat your oven to 180°C (350°F), or 160°C (320°F) if using a fan-assisted oven.

Prepare the Topping:

  • Lay out the pineapple rings and cherries on a tray lined with absorbent paper towels or a clean tea towel. Gently pat them dry to reduce excess moisture.
  • Pour the melted butter into a round cake tin measuring 23 cm (9 inches) in diameter and at least 5 cm (2 inches) deep. Avoid using a springform pan to prevent leakage. Use a brush to spread the butter evenly across the base and sides of the pan.
  • Sprinkle the brown sugar over the base, lightly distributing it using the same brush.
  • Place a single pineapple ring in the center of the pan, and arrange additional rings—halved or whole—around it. Decorate with cherries, pressing one into the middle of each ring or as desired. Firmly press the fruit into the sugar-butter layer to ensure vibrant color upon unmolding.

Make the Batter:

  • In a medium bowl, whisk together the flour, baking powder, baking soda, and salt.
  • In a separate bowl, combine the milk, sour cream, reserved pineapple juice, and vanilla extract. Mix until smooth.
  • Using a third bowl, cream the softened butter with the granulated sugar. Beat with a handheld mixer on speed 7 for approximately 2 minutes until light and fluffy.
  • Add the eggs one at a time, beating for about 20 seconds after each addition until fully incorporated.
  • Begin combining the dry and wet mixtures into the butter base. Start by folding in one-third of the flour mixture using a rubber spatula. Then add half of the milk mixture and fold gently. Continue by incorporating another third of the flour mixture, followed by the rest of the milk mixture, and finally the remaining flour. Fold in the chopped leftover pineapple.
  • Gently spoon the finished batter into the prepared cake pan, spreading it evenly over the arranged fruit and smoothing the top.
  • Bake uncovered for 30 minutes. Then, loosely cover the cake with foil and return to the oven for an additional 15 minutes, or until a skewer inserted into the center comes out clean.

Turn Out the Cake:

  • Once baked, remove the cake from the oven and allow it to rest in the pan for 20 minutes.
  • Run a knife along the edge of the cake to loosen it. Place a serving plate or platter over the pan, and carefully invert. Tap or gently shake the pan, then lift it away to reveal the fruit-topped surface.
  • Allow the cake to cool completely before slicing and serving.
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Notes

  • Use only pineapple canned in juice, not syrup, as the syrup will overly sweeten the cake and cannot be used for flavoring the batter.
  • Standard can sizes in Australia are 430g and 225g; purchasing one of each provides sufficient quantity, with extra for folding into the batter.
  • If maraschino cherries are unavailable, glacé cherries are a suitable substitute.
  • Ensure butter is at the correct softness—pliable but not greasy—for effective creaming. Ideal temperature is around 18°C (64°F).
  • Eggs should be at room temperature for optimal mixing; submerge in warm tap water for 5 minutes if cold.
  • Firmly pressing down the fruit before baking ensures more vivid coloring and cleaner definition after baking.
  • For an extra glossy finish, brush the cooled fruit with warmed corn syrup or diluted apricot jam.
  • Store the cake in the refrigerator for up to 5 days. Bring to room temperature before serving for best texture and flavor.