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Fresh Pineapple Upside Down Cake

Pineapple Upside Down Cake using fresh pineapple, and a yellow cake mix because why not?! Make this recipe with two 8-inch rounds or 24 cupcakes.

Course: Dessert
Author: Kami | NoBiggie.net
Ingredients
  • 1/3 cup butter melted
  • 1 ¼ cup packed brown sugar
  • ½ fresh pineapple rind removed, sliced and core removed (may use 20 oz. can pineapple rings and juice in cake mix)
  • Maraschino cherries drained
  • 1 box yellow cake mix mixed according to directions with oil and eggs but substitute pineapple juice for water (if using canned pineapple)
Instructions
Instructions for two 8-inch round cakes:
  1. Preheat your oven to 350 F. Grease two 8-inch cake pans.

  2. Melt the butter in the microwave. Add the brown sugar to the butter and mix the two together.

  3. Pour the butter brown sugar mixture evenly into the bottom of two greased 8-inch round cake pans (or one 9x13 pan).

  4. Place pineapple rings and maraschino cherries into the bottom of the pan in a decorative pattern.

  5. Prepare the cake mix batter as directed on the box. Gently pour the cake batter over the pineapple and cherries.

  6. Bake for 35 - 40 minutes or less. Insert a toothpick to check for doneness. If the tooth pick comes out clean, you know the cake is done.

  7. To serve the cake, run a knife around the edge of the cake. Place a plate wider than the pan over the top of the pan, and with two hands flip the cake over onto the plate. Scrap out any excess caramel over the top of the cake.

  8. Serve warm with sweetened cold whipped cream.

Recipe Notes
  • Instructions for making cupcakes:
  • Preheat your oven to 350 F. Grease the cups of two cupcake pans.
  • Prepare the pineapple: cut the pineapple into chunks (not rings)
  • Prepare the cake mix batter: as directed on the box, mix together the cake mix. 
  • Combine the butter and brown sugar: Melt the butter in the microwave. Add the brown sugar to the butter and mix the two together.
  • Add 1 teaspoon of the butter brown sugar mixture to the cups of both cupcake pans. You will most likely have excess of this mixture.
  • Place 3-4 chunks of pineapple into each individual cup, on top of the butter and brown sugar mixture.
  • Using an ice cream / cookie scoop, add the cake batter to each cup over the pineapple chunks and the butter brown sugar mixture. Fill each cup 2/3rds full.
  • Bake: Bake for 18-21 minutes or less depending on your oven. Insert a toothpick to check for doneness. If the tooth pick comes out clean, you know the cupcakes are done.
  • To serve the cupcakes, carefully run a knife around the edge of each individual cupcake. Using a spoon, carefully lift each one out of the pan and move them to a serving plate. Scrap out any excess caramel and spoon over the top of the cupcakes.
  • Serve: Serve warm with sweetened cold whipped cream and a maraschino cherry on top or serve with vanilla ice cream.