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Pioneer Woman Pineapple Upside-Down Cake

Pioneer Woman Pineapple Upside-Down Cake - recipe card
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A moist, tender vanilla cake crowned with caramelized pineapple rings and maraschino cherries. This classic upside-down cake features a rich buttery brown sugar glaze that seeps into the cake as it bakes, creating a perfectly balanced sweet and tangy dessert.

Ingredients

Scale
  • 1/4 cup unsalted butter, melted
  • 1/2 cup packed light brown sugar
  • 4 slices canned pineapple rings, drained (reserve 2 tbsp juice)
  • 4 maraschino cherries, stems removed
  • 3/4 cup all-purpose flour
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon baking soda
  • 1/4 teaspoon kosher salt
  • 1/4 cup unsalted butter, softened (for cake batter)
  • 1/2 cup granulated sugar
  • 1 large egg, room temperature
  • 1/2 teaspoon vanilla extract
  • 1/4 cup buttermilk, room temperature
  • 2 tablespoons reserved pineapple juice

Instructions

  1. Position a rack in the center of the oven and preheat to 350°F (177°C). Place a 9-inch cast-iron skillet or 8×8-inch metal baking pan on a baking sheet to catch any drips. The pan should be oven-safe and at least 2 inches deep.
  2. In a small microwave-safe bowl, melt 1/4 cup unsalted butter in the microwave in 15-second bursts until fully liquid, about 30 seconds total. Pour the melted butter into the bottom of your chosen pan, tilting to coat evenly. Sprinkle 1/2 cup packed light brown sugar evenly over the butter, patting down gently with your fingers to form an even layer.
  3. Arrange the 4 pineapple rings in a single layer over the brown sugar mixture, spacing them evenly — one in each quadrant of the pan. Place a maraschino cherry in the center of each pineapple ring, gently pressing it into the butter-sugar mixture. Set the pan aside.
  4. In a medium bowl, whisk together 3/4 cup all-purpose flour, 1/2 teaspoon baking powder, 1/4 teaspoon baking soda, and 1/4 teaspoon kosher salt. Whisk for 10 seconds to evenly distribute the leaveners and salt. Set aside.
  5. In a large bowl, using a hand mixer or stand mixer fitted with the paddle attachment, beat 1/4 cup softened unsalted butter and 1/2 cup granulated sugar on medium-high speed until pale and fluffy, about 3 minutes, scraping down the sides as needed. The mixture should look light and increased in volume.
  6. Add 1 large room-temperature egg and 1/2 teaspoon vanilla extract to the butter-sugar mixture. Beat on medium speed until fully incorporated, about 30 seconds, scraping the bowl once. The batter may look slightly separated at this point; that’s normal.
  7. In a small measuring cup, combine 1/4 cup buttermilk and 2 tablespoons reserved pineapple juice. Stir briefly. With the mixer on low speed, add the flour mixture in three additions, alternating with the buttermilk mixture in two additions, beginning and ending with flour. Mix just until the flour disappears — about 15 seconds total. Do not overmix, or the cake will be tough.
  8. Pour the batter evenly over the pineapple rings in the pan, using a small offset spatula to spread it gently to the edges. The batter should barely cover the pineapple rings. Do not shake or tap the pan, or you may dislodge the fruit arrangement.
  9. Bake the cake for 28 to 32 minutes, rotating the pan halfway through, until the top is golden brown and a wooden skewer inserted into the center of the cake (not through a pineapple ring) comes out clean or with a few moist crumbs attached. The cake will pull away slightly from the sides of the pan.
  10. Remove the pan from the oven and place on a wire rack. Let the cake cool in the pan for exactly 5 minutes — no longer, or the caramel will harden and stick. Run a thin knife or offset spatula around the edge of the cake to loosen it from the pan.
  11. Place a large serving plate or cake stand upside down over the pan. Using oven mitts, carefully invert the pan and plate together, then lift the pan off. If any fruit or caramel sticks to the pan, gently scrape it off and reposition it on the cake. The caramel will be very hot — allow the cake to cool for at least 20 minutes before slicing.
  12. Serve the cake warm or at room temperature, cut into 4 equal squares or wedges. A dollop of lightly sweetened whipped cream or a scoop of vanilla ice cream complements the caramelized pineapple beautifully.

Notes

Store leftover cake tightly covered with plastic wrap or in an airtight container at room temperature for up to 2 days. For longer storage, refrigerate for up to 5 days (bring to room temperature before serving for best texture). To freeze, wrap individual slices tightly in plastic wrap and then foil, and freeze for up to 3 months. Thaw overnight in the refrigerator and warm individual slices in a 300°F (149°C) oven for 5-7 minutes or microwave for 15-20 seconds. For the best caramel release, do not exceed the 5-minute rest time before inverting. If the cake sticks, place the pan back on the burner over low heat for 30 seconds to remelt the caramel, then invert again.

Nutrition

Keywords: pineapple upside-down cake, Pioneer Woman recipe, classic pineapple cake, upside down cake, butter cake, pineapple dessert, maraschino cherry cake, caramelized pineapple cake, American dessert, easy cake recipe, cast iron cake, retro cake

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