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Pineapple Upside-Down Pumpkin Gingerbread

A delightful fusion dessert combining the classic pineapple upside-down cake with warm gingerbread and pumpkin flavors. This unique cake features a caramelized pineapple topping and a moist, spiced gingerbread-pumpkin cake base.

8 servings
2 hr 20 min
Published October 4, 2025

Ingredients

  • •1 spray Nonstick vegetable oil spray
  • •⅔ cup golden brown sugar
  • •½ cup unsalted butter
  • •2 tablespoons pineapple juice concentrate
  • •1 teaspoon light molasses
  • •1 whole pineapple
  • •2 cups all purpose flour
  • •2 teaspoons baking soda
  • •2 teaspoons baking powder
  • •1¼ teaspoons ground cinnamon
  • •¾ teaspoon ground ginger
  • •½ teaspoon salt
  • •½ cup unsalted butter
  • •1 cup sugar
  • •2 whole eggs
  • •½ cup light molasses
  • •½ cup pumpkin puree
  • •½ cup boiling water
  • •1 cup whipped cream

Cooking Instructions

  1. 1.

    Preheat oven to 350°F. Spray 9x9x2-inch metal baking pan with nonstick spray. Combine sugar, butter, pineapple juice concentrate, and molasses in heavy small saucepan. Bring to boil over medium heat, whisking until sugar dissolves and syrup is smooth; boil 1 minute. Pour evenly into prepared pan.

    10 min

  2. 2.

    Cut off one 1/3-inch-thick round from pineapple; cut out core. Place round in syrup in pan. Stand pineapple on end. Cut lengthwise into 1/3-inch-thick slices. Using 3 round cutters of different sizes, cut out rounds from pineapple slices, avoiding core. Arrange rounds close together in single layer in free-form design in syrup.

    15 min

  3. 3.

    Whisk first 6 ingredients in medium bowl. Beat butter in large bowl until fluffy. Add sugar and beat to blend. Beat in eggs, 1 at a time. Beat in molasses, then pumpkin. Beat in dry ingredients just until blended, occasionally scraping down sides of bowl. Beat in 1/2 cup boiling water. Pour batter evenly into pan.

    15 min

  4. 4.

    Bake cake until tester inserted into center comes out clean, about 50 minutes. Cool cake in pan 45 minutes. Place platter over pan and invert. Let stand 5 minutes. Gently lift off pan. Serve cake warm or at room temperature with whipped cream.

    100 min

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