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Pineapple Upside-Down Cupcakes Recipe

Pineapple Upside-Down Cupcakes Recipe


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4.5 from 34 reviews

  • Total Time: 40 minutes
  • Yield: 24 1x

Description

Pineapple Upside-Down Cupcakes bring classic retro charm to modern dessert tables with individual-sized nostalgia. Sweet caramelized pineapple tops moist vanilla cake, creating a delightful twist on traditional skillet-baked treats that will make you crave another bite.


Ingredients

Scale

Main Ingredients:

  • 1 package (18.25 ounces / 517 grams) pineapple cake mix
  • 3 large eggs
  • ½ cup vegetable oil
  • 1 ½ cups reserved pineapple juice

Topping Ingredients:

  • ½ cup melted butter
  • 1 ½ cups brown sugar
  • 1 can (20 ounces / 567 grams) crushed pineapple, well-drained
  • 24 maraschino cherries

Optional Finishing Ingredient:

  • 1 tablespoon confectioners’ sugar for dusting

Instructions

  1. Preheat the oven to 350°F (175°C) and generously coat 24 muffin cups with non-stick cooking spray, ensuring complete coverage.
  2. Drizzle of melted unsalted butter into each muffin cup, then sprinkle of brown sugar evenly across the butter layer. Gently place a maraschino cherry at the center of each cup and carefully distribute crushed pineapple around it, pressing softly to create an even, attractive base.
  3. In a large mixing bowl, combine the pineapple cake mix, reserved pineapple juice, large eggs, and vegetable oil. Blend the ingredients using an electric mixer, beginning at low speed for 30 seconds to incorporate, then increasing to medium speed for 2 minutes until the batter becomes smooth and well-integrated.
  4. Distribute the prepared batter evenly among the muffin cups, filling each approximately two-thirds full to allow room for rising during baking.
  5. Transfer the muffin tins to the preheated oven and bake for 18-22 minutes, checking doneness by inserting a toothpick into the center of a cupcake – it should emerge clean with no wet batter attached.
  6. Remove from the oven and let the cupcakes rest in the pan for 5 minutes. Carefully run a knife around the edges to loosen, then invert onto a wax paper-lined baking sheet, allowing the pineapple and cherry topping to settle naturally.
  7. Before serving, optionally dust the cupcakes with a light sprinkle of confectioners’ sugar for an elegant finishing touch and added sweetness.

Notes

  • Flip the cupcakes immediately after baking to prevent sticking and maintain the beautiful caramelized topping’s intricate design.
  • Ensure pineapple pieces are thoroughly drained to avoid excess moisture that could compromise the cupcake’s texture.
  • Room temperature ingredients blend more smoothly, creating a more consistent and tender cake batter.
  • Store leftover cupcakes in an airtight container at room temperature for maximum freshness, consuming within 2-3 days.
  • Customize the recipe by substituting maraschino cherries with fresh dark cherries for a more natural, vibrant flavor profile.
  • Cold ingredients can create lumpy batter, so let eggs and juice sit out 30 minutes before mixing for optimal results.
  • Prep Time: 20 minutes
  • Cook Time: 20 minutes
  • Category: Desserts, Snacks
  • Method: Baking
  • Cuisine: American

Nutrition

  • Serving Size: 24
  • Calories: 228 kcal
  • Sugar: 20g
  • Sodium: 265mg
  • Fat: 10g
  • Saturated Fat: 2g
  • Unsaturated Fat: 7g
  • Trans Fat: 0g
  • Carbohydrates: 34g
  • Fiber: <1g
  • Protein: 3g
  • Cholesterol: 37mg