Amazing Pineapple Upside-Down Cupcakes Recipe

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Amazing Pineapple Upside-Down Cupcakes Recipe

I made this with a few tweaks, but it was AMAZING. I can’t believe I’ve never thought to make these before. Sweet, soft, moist, and sturdy; the perfect pineapple upside down experience.
1/2 cup buttermilk –> 1/4 cup reserved pineapple juice, 1/4 cup buttermilk
6 tbsp melted butter–> 6 tbsp softened butter, smeared around the bottom and sides of each cup
3/4 cup brown sugar–> 1/4 tsp white sugar under the 1 tbsp brown sugar. Packed along the bottom and up sides of the tin.

How To Make It

Sweet and simple pineapple upside down-cupcakes made entirely from scratch (don’t worry, they’re easy!). With fluffy vanilla cupcake bases topped off with caramelized pineapple and maraschino cherries, these are a great new way to enjoy a classic recipe!



  • 6 Tablespoons butter melted
  • 3/4 cup brown sugar
  • 20 oz +8 oz can pineapple chunks in pineapple juice or substitute fresh pineapple
  • 12 Maraschino cherries


  • 1/2 cup unsalted butter softened to room temperature
  • 3/4 cup sugar
  • 2 eggs
  • 1 teaspoon vanilla extract
  • 1 1/2 cups all-purpose flour
  • 1 1/2 teaspoons baking powder
  • 1/4 teaspoon salt
  • 1/2 cup buttermilk


  1. Preheat oven to 350F and lightly spray a 12-count cupcake tin with baking spray.
  2. Evenly divide butter into the bottom of each cupcake well.
  3. Sprinkle each well with 1 Tablespoon of brown sugar.
  4. Rim the bottom of each pan by laying 4 pineapple chunks in a flower pattern over the butter and brown sugar.
  5. Press a Maraschino cherry into the center of each “flower”. Set aside.


  1. Prepare your cupcakes by beating together butter and sugar in a medium-sized bowl until creamy and well-combined.
  2. Add eggs, beating one at a time until combined.
  3. Stir in vanilla extract.
  4. In a separate bowl, whisk together flour, baking powder, and salt.
  5. Alternate adding flour and buttermilk, starting and ending with flour and mixing until just combined after each addition (I prefer to do this part by hand with a spatula to be sure not to over-mix).
  6. Evenly divide the cupcake batter into your prepared pan. The batter will be thick, so use a spoon to spread it evenly into each cupcake well. Fill each cupcake well all the way to the top.
  7. Bake on 350F for 22-25 minutes.
  8. Remove, allow to cool for 5 minutes, and then place a wire cooling rack over the cupcake tin, covering each cupcake.
  9. Carefully, using potholders as the tin will be very hot, keep the cooling rack pressed against the tin and invert. Lift the muffin tin, the cupcakes should release easily.
  10. Allow to cool before serving. These pineapple upside down cupcakes taste great served warm with vanilla ice cream!