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Classic Pineapple Upside-Down Skillet Cake

pineapple upside-down skillet cake - featured image

A quick and easy homemade pineapple upside-down skillet cake with a perfect caramelized topping, moist crumb, and tropical twist. Ideal for any occasion and a crowd-pleaser for all ages.

Ingredients

Scale
  • 4 tablespoons unsalted butter, softened
  • ⅓ cup packed brown sugar (preferably dark brown)
  • 1 can pineapple rings (about 8 ounces), drained (or fresh pineapple slices, patted dry)
  • 8 maraschino cherries
  • 1 cup all-purpose flour (125 grams)
  • 1 teaspoon baking powder
  • ¼ teaspoon salt
  • ⅔ cup granulated sugar (130 grams)
  • 1 large egg, room temperature
  • ½ cup whole milk (120 ml) (or almond milk for dairy-free)
  • 1 teaspoon vanilla extract
  • 3 tablespoons vegetable oil

Instructions

  1. Preheat the oven to 350°F (175°C).
  2. Place softened butter and brown sugar into a 10-inch oven-safe skillet. Warm over medium heat, stirring constantly until butter melts and sugar dissolves into a smooth, bubbling caramel (3 to 5 minutes). Avoid burning.
  3. Remove skillet from heat. Arrange pineapple rings on top of the caramel in a single layer. Place a maraschino cherry in the center of each ring and in gaps between slices.
  4. In a medium bowl, whisk together flour, baking powder, and salt.
  5. In another bowl, whisk granulated sugar and egg until smooth and pale. Add milk, vanilla extract, and vegetable oil; mix until combined.
  6. Slowly add dry ingredients to wet ingredients, stirring gently just until incorporated. Avoid overmixing.
  7. Pour batter evenly over the pineapple and caramel in the skillet. Spread gently with an offset spatula or spoon.
  8. Bake in the oven for 35 to 40 minutes. Check doneness with a toothpick; it should come out clean or with a few moist crumbs.
  9. Let the cake rest in the skillet for 10 minutes after baking. Place a large plate or cutting board over the skillet and flip in one smooth motion to invert the cake.
  10. Serve warm or at room temperature, optionally with vanilla ice cream.

Notes

Use firm pineapple rings to prevent breaking. Pat fresh pineapple dry to avoid sogginess. Dark brown sugar and real unsalted butter create richer caramel flavor. Avoid overmixing batter to keep cake tender. Watch caramel closely to prevent burning. Well-seasoned cast iron skillet helps prevent sticking. If edges brown too fast, tent with foil.

Nutrition

Keywords: pineapple upside-down cake, skillet cake, caramelized topping, easy dessert, tropical dessert, homemade cake