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Homemade pineapple upside down cupcakes topped with a glossy cherry and caramelized pineapple ring, on a white plate with more cupcakes blurred in the background.

Pineapple Upside Down Cupcakes

5 from 1 vote
Perfect for parties, these Pineapple Upside Down Cupcakes deliver retro charm and modern convenience. Each cupcake features a caramelized pineapple ring with a cherry center and moist vanilla cake.
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Prep Time 20 minutes
Cook Time 20 minutes
Cooling Time 10 minutes
Total Time 50 minutes
Servings: 12 cupcakes
Course: Dessert
Cuisine: American
Calories: 220
Ingredients Equipment Method Nutrition Notes

Ingredients
  

For the Caramelized Topping:
  • 6 tablespoon Unsalted butter - Melted
  • ⅔ cup Brown sugar - Light or dark
  • 6 Pineapple rings - Cut in halves to fit muffin cups
  • 12 Maraschino cherries - Drained
For the Cupcake Batter:
  • 1½ cups All-purpose flour
  • ¾ cup Granulated sugar
  • ½ cup Unsalted butter - Softened
  • 2 Large eggs - Room temperature
  • 1½ teaspoon Baking powder
  • ¼ teaspoon Salt
  • 1 teaspoon Vanilla extract
  • ½ cup Milk - Whole preferred
Optional Flavor Boosters:
  • 2 tablespoon Pineapple juice - Replace part of milk
  • ½ teaspoon Coconut extract - Adds tropical flair
  • ½ teaspoon Rum extract - For adult flavor
  • 1 teaspoon Lemon zest - Brightens flavor

Equipment

  • 12-cup muffin tin (Well-greased)
  • Electric mixer (Hand or stand mixer)
  • Large mixing bowl
  • Wire cooling rack (For flipping and cooling cupcakes)
  • Knife (For loosening cupcake edges)
  • Can opener (For canned pineapple)

Method
 

  1. Preheat oven to 350°F and grease a 12-cup muffin tin thoroughly.
  2. Mix melted butter with brown sugar and place in muffin cups. Add pineapple rings and cherries.
  3. Cream butter and sugar, add eggs and vanilla, then mix in dry ingredients alternately with milk.
  4. Spoon the batter over the fruit in muffin cups, filling each about ⅔ full.
  5. Bake for 18–22 minutes until golden and a toothpick comes out clean.
  6. Cool 5 minutes, run a knife around edges, flip onto a rack, and let sit 2 minutes before lifting.

Nutrition

Serving: 1CupcakeCalories: 220kcalCarbohydrates: 30gProtein: 2gFat: 10gSaturated Fat: 6gPolyunsaturated Fat: 0.5gMonounsaturated Fat: 2.5gCholesterol: 40mgSodium: 95mgPotassium: 70mgFiber: 0.5gSugar: 20gVitamin A: 300IUVitamin C: 2mgCalcium: 40mgIron: 0.8mg

Notes

Nutrition information is automatically calculated and should be considered an approximation. Actual values may vary based on specific ingredients used and portion sizes.

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