Freshly baked Pineapple Upside Down Cupcakes with maraschino cherries on a cooling rack

Delicious Pineapple Upside Down Cupcakes Recipe | Easy and Quick

These pineapple upside down cupcakes are the perfect treat for family gatherings, parties, or even a special addition to lunchboxes. This simplified version of a classic dessert brings all the tropical flavors to your table with minimal effort. Submitted by Bri and tested by the Allrecipes Test Kitchen, this recipe promises a delightful experience for your taste buds.

The Best Pineapple Upside Down Cupcakes

Notes on Ingredients

To create these delectable cupcakes, you’ll need a mix of simple ingredients that blend together harmoniously:

  • Cooking Spray: To prevent sticking and ensure easy removal.
  • Butter: Melted, for that rich, buttery base.
  • Brown Sugar: Adds a deep, caramelized sweetness.
  • Maraschino Cherries: Bright and cheerful, these are the stars of the topping.
  • Crushed Pineapple: The juicy core of this tropical delight.
  • Pineapple Cake Mix: Such as Duncan Hines Pineapple Supreme for ease.
  • Pineapple Juice, Vegetable Oil, and Eggs: Essential for the cake batter.

How to Make Pineapple Upside Down Cupcakes

  1. Preheat and Prep: Begin by preheating your oven to 350°F (175°C). Adjust an oven rack to the middle position. Spray 24 muffin cups generously with cooking spray.
  2. Create the Base: Into each muffin cup, spoon 1 teaspoon of melted butter followed by 1 tablespoon of brown sugar. Place a maraschino cherry at the center of the brown sugar in each cup. Top with a heaping tablespoon of crushed pineapple, pressing it down to create an even layer.
  3. Prepare the Batter: In a large mixing bowl, combine the pineapple cake mix, pineapple juice, vegetable oil, and eggs. Use an electric mixer on low speed to moisten the ingredients for about 30 seconds, then increase to medium speed and mix for an additional 2 minutes.
  4. Fill the Cups: Pour the prepared batter into the muffin cups, filling them to the top without overfilling.
  5. Bake: Place the muffin tin in the preheated oven and bake until a toothpick inserted into the center comes out clean, approximately 20 minutes.
  6. Cool and Serve: Allow the cupcakes to cool for at least 5 minutes before inverting them onto a wax paper-lined surface. Serve with the pineapple and cherry side up, and dust lightly with confectioners’ sugar if desired.

How to Serve Pineapple Upside Down Cupcakes

These cupcakes are best served warm, fresh from the oven, but they can also be enjoyed at room temperature. Their bright and festive appearance makes them perfect for parties, potlucks, or as a delightful end to any meal.

How to Store Pineapple Upside Down Cupcakes

Store any leftover cupcakes in an airtight container in the refrigerator for up to 3 days. Reheat them slightly before serving to enhance their flavors and texture.

Nutrition information

NutrientAmount per serving% Daily Value*
Calories215.32 kcal11%
Total Fat9.64 g14%
Carbs32.22 g12%
Sugars25.77 g29%
Protein2.09 g4%
Sodium118.43 mg6%
Fiber0.49 g2%
Saturated Fat4.19 g21%
Trans Fat0 g
Monounsaturated Fat2.77 g
Polyunsaturated Fat1.62 g
Cholesterol44.21 mg15%
Calcium40.58 mg5%
Magnesium6.76 mg2%
Potassium70.57 mg2%
Iron0.5 mg4%
Zinc0.13 mg1%
Phosphorus16.42 mg2%
Vitamin A47.18 mcg6%
Vitamin C3.63 mg5%
Thiamin B10.03 mg3%
Riboflavin B20.04 mg3%
Niacin B30.11 mg1%
Vitamin B60.05 mg3%
Folic Acid B96.86 mcg3%
Vitamin B120.06 mcg3%
Vitamin D0.13 mcg3%
Vitamin E0.54 mg5%
Vitamin K4.11 mcg6%
Nutrition Information for Pineapple Upside Down Cupcakes

*Percent Daily Values are based on a 2,000 calorie diet. Your daily values may be higher or lower depending on your calorie needs.

FAQs About Pineapple Upside Down Cupcakes

Can I use fresh pineapple instead of canned?

Yes, you can use fresh pineapple. Just make sure to finely chop it and drain any excess juice to prevent the cupcakes from becoming too soggy.

Can I make these cupcakes ahead of time?

Absolutely! You can prepare the cupcakes a day in advance. Just store them in the refrigerator and reheat slightly before serving.

Can I freeze these cupcakes?

Yes, you can freeze them. Wrap each cupcake individually in plastic wrap and store them in a freezer-safe bag for up to 2 months. Thaw and reheat before serving.

Pineapple Upside Down Cupcakes

The Best Pineapple Upside Down Cupcakes

Discover the best Pineapple Upside Down Cupcakes recipe! Easy to make, these cupcakes are perfect for family gatherings or lunchbox treats. Try this delightful dessert today!
Temps de préparation 20 minutes
Temps de cuisson 20 minutes
Additional Time 5 minutes
Temps total 45 minutes
Type de plat Dessert Plate
Cuisine American
Portions 24 Cupcakes
Calories 215.32 kcal


  • cooking spray
  • ½ cup butter melted
  • 1 ½ cups brown sugar
  • 24 maraschino cherries
  • 1 20 ounce can crushed pineapple
  • 1 15.25 ounce package pineapple cake mix (such as Duncan Hines Pineapple Supreme)
  • 1 ⅓ cups pineapple juice
  • cup vegetable oil
  • 3 large eggs
  • 1 tablespoon confectioners’ sugar for dusting or as needed


  • Preheat the oven to 350 degrees F (175 degrees C). Move an oven rack to the middle of the oven. Spray 24 muffin cups with cooking spray.
  • Spoon 1 teaspoon melted butter into the bottom of each sprayed muffin cup. Spoon 1 tablespoon brown sugar into each muffin cup. Press a maraschino cherry into the center of the brown sugar in each muffin cup. Spoon a heaping tablespoon of crushed pineapple on top and compact it with the back of a spoon into an even layer.
  • Mix pineapple cake mix, pineapple juice, vegetable oil, and eggs in a large bowl with an electric mixer on low speed until moistened, about 30 seconds. Increase speed to medium; mix for 2 minutes.
  • Pour batter into the muffin cups, filling them to the top; do not overfill.
  • Bake in the preheated oven until a toothpick inserted into the center of a cupcake comes out clean, about 20 minutes.
  • Line a work surface with waxed paper. Allow cupcakes to cool at least 5 minutes before inverting muffin cups onto the waxed paper; serve with pineapple and cherry sides up. Sprinkle cupcakes lightly with confectioners’ sugar before serving.
Keyword Cupcakes, Party Treats, Pineapple
Pineapple Upside Down Cupcakes with a golden topping of caramelized pineapple and cherries

Enjoy your baking adventure with these Pineapple Upside Down Cupcakes and delight in the tropical sweetness they bring to any occasion!

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