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Pineapple Upside Down Cupcakes With a Clean Easy Flip

Pineapple upside-down cupcakes on a cooling rack, with one cupcake cut open showing a split cherry center.

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Pineapple upside down cupcakes with a clean, easy flip and a glossy caramel topping.

Tender buttermilk cupcakes baked right over pineapple and cherries.

Ingredients

Scale
  • For the topping
  • 6 Tablespoons (85 g) salted butter, melted
  • 12 Tablespoons (150 g) light brown sugar (3/4 cup), firmly packed
  • 2 1/3 cups (438 g) pineapple chunks, drained and patted dry
  • 12 maraschino cherries, drained
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  • For the cupcakes
  • 1/2 cup (113 g) unsalted butter, softened to room temperature
  • 3/4 cup (150 g) granulated sugar
  • 2 large eggs (room temperature preferred)
  • 1 teaspoon vanilla extract
  • 1 1/2 cups (187 g) all-purpose flour
  • 1 1/2 teaspoons baking powder
  • 1/4 teaspoon table salt
  • 1/2 cup (118 ml) buttermilk

Instructions

  1. Preheat oven to 350°F (175°C).
  2. Divide melted salted butter into the bottom of each cupcake well and lightly brush the sides with butter.
  3. Sprinkle 1 tablespoon packed brown sugar evenly into the bottom of each cupcake well.
  4. Arrange 4 pineapple chunks in a flower pattern over the butter and sugar, then press a cherry into the center of each.
  5. Beat softened butter and granulated sugar until light and fluffy.
  6. Add eggs and vanilla extract and beat until smooth.
  7. Whisk together flour, baking powder, and salt in a separate bowl.
  8. Alternate adding the flour mixture and buttermilk, starting and ending with flour, stirring gently until just combined.
  9. Divide batter evenly into the pan, filling each well to the rim; gently spread the thick batter.
  10. Set the tin on a foil-lined rimmed baking sheet and bake 22–25 minutes, until a toothpick comes out clean or with moist crumbs.
  11. Cool in the pan for 5 minutes, then run a thin knife around the edges to loosen.
  12. Place a wire rack over the pan and invert in one smooth motion; lift the tin straight up.
  13. Cool slightly, then serve warm (great with vanilla ice cream).

Notes

  • Drain and pat the pineapple dry to prevent soggy bottoms and overflow.
  • Flip after a 5-minute rest for the cleanest release.
  • Skip cupcake liners for this recipe; use a well-buttered pan instead.
  • Nutrition values are estimates and vary by ingredients and serving size.

Nutrition