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Pineapple Upside-down Cupcakes - by Glorious Treats

Pineapple Upside-down Cupcakes

Course: Dessert
Cuisine: American
Keyword: pineapple cupcakes, pineapple upside-down cupcakes
Prep Time: 1 hour
Cook Time: 25 minutes
Total Time: 1 hour 25 minutes
Servings: 12
Calories: 612kcal
Make this recipe using a jumbo cupcake pan for individual servings, or in a 9"x13" pan for a classic cake.
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Brown Sugar Glaze

  • 6 tablespoons Challenge butter
  • 2 tablespoons light corn syrup
  • 1 cup packed brown sugar
  • 12 canned pineapple slices you'll need 2 cans
  • 6 maraschino cherries each cut in half


  • 2 1/2 cups flour
  • 1 teaspoon baking powder
  • 1/2 teaspoon baking soda
  • 1/2 teaspoon salt
  • 3 eggs
  • 2 cups sugar
  • 1 cup oil vegetable, canola, etc
  • 2 teaspoon vanilla extract
  • 1 cup sour cream any fat content


  • Prepare 2 JUMBO cupcake pans by greasing the molds, and then lining just the bottoms with paper liners. I used Jumbo cupcake liners, and cut them down so the liner just fills the bottom (and up the side just a bit). The liner will just help keep the pineapple and glaze in tact as you remove the cakes from the pan.
  • Prepare the pineapple slices by cutting out a notch of pineapple (as pictured above). This allows the pineapple to sit nicely in the bottom of the cupcake pan. Cut one pineapple slice and then place it in your pan to get an idea of the size piece you need to remove.
  • Prepare the brown sugar glaze by combining the butter, corn syrup and brown sugar in a small saucepan. Heat until the butter and sugar are melted, and the mixture is smooth. Set aside to cool.
  • Prepare the cake batter. In a large bowl add the flour, baking powder, baking soda and salt. Whisk to combine, then set aside.
  • In the bowl of an electric mixer, add eggs and beat 15 seconds. Add the sugar, and continue to beat until the mixture thickens and is a light in color.
  • While mixing on low speed, add the oil and vanilla and mix until well blended. Add sour cream, and mix to combine.
  • Slowly add the flour mixture and mix just until the flour is fully incorporated.
  • Assemble cakes for baking by adding 1-1/2 tablespoons of the brown sugar mixture to the bottom of each (lined) cupcake mold. Top glaze with a slice of pineapple and half of a maraschino cherry.
  • Pour (or scoop) the cake batter on top of each pineapple slice, filling each cupcake mold 2/3 - 3/4 full (do your best to evenly divide the batter between each cupcake).
  • Bake cupcakes in a preheated 350*F oven for about 25 minutes (or until a toothpick inserted in the center of a cake comes out clean, or with a few moist crumbs).
  • Allow cakes to cool about 5 minutes, then run a knife along the edges of each cake to loosen it from the pan. Flip over the entire pan, onto a baking sheet. Remove the paper liner, and serve.
  • Cakes can be served warm, or at room temperature.


If you only have one jumbo cupcake pan, simply bake one pan at a time, then repeat the assembly for the second batch.
If making this recipe as one large cake, lightly grease the pan, and line the bottom with parchment paper. Baking time is not listed because I have not made the recipe in a 9"x13" pan. I would estimate 45-50 minutes, but you will know the cake is done when the top is a deep golden brown, the center of the cake has a slight dome, and a toothpick inserted in the center comes out clean. After baking, cool at 15 minutes. Run a knife along the edges of the pan to loosen cake, and turn pan upside down over a baking sheet or platter. Allow the pan to remain (upside down) on the cake a minute, then carefully remove.


Calories: 612kcal | Carbohydrates: 85g | Protein: 5g | Fat: 30g | Saturated Fat: 8g | Cholesterol: 66mg | Sodium: 219mg | Potassium: 165mg | Fiber: 2g | Sugar: 64g | Vitamin A: 382IU | Vitamin C: 6mg | Calcium: 78mg | Iron: 2mg