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You’ll love this delightful twist on a classic dessert with these pineapple upside down cupcakes! Bursting with tropical flavors, these mini treats feature a moist vanilla cake base topped with caramelized pineapple and a bright cherry, making them the perfect addition to any BBQ or gathering. Not only are they incredibly easy to whip up using a simple cake mix, but their individual servings make them a fun and portable option for sharing.
Indulge in these easy pineapple upside down cupcakes. Perfectly delicious and sweet as well as wonderfully moist, they’re an absolute must-try for your next dessert.
You might also like pie iron pineapple upside down cakes, this pineapple coconut lush dessert, or these irresistible spiced pineapple rum toddies.
Why You’ll Love It
Simple to make: Using a cake mix instead of making the whole thing from scratch cuts down on prep time and makes the recipe easy.
Tastes so good: The sweetness of the pineapple and cherries is so good with the light, moist cake.
Great for any occasion: These cupcakes are ideal for any occasion, whether you just want to surprise the family after dinner or you’re planning a party.
Pineapple Upside Down Cupcakes Ingredients
A complete list of ingredients and amounts can be found in the recipe card below.
Yellow cake mix: You can use a pineapple cake mix instead if you can find one.
Maraschino cherries: To add a pop of color and distinctive sweet flavor.
Pineapple slices: Canned pineapple is perfect for this recipe and you will use both the pineapple pieces and the juice from the can.
Light brown sugar: For sweetness.
Eggs: To bind the cake batter.
How to Make Pineapple Upside Down Cupcakes with Cake Mix
For more detailed instructions with weights and measurements, jump to the printable recipe card.
Make the cake batter: Combine cake mix with eggs, oil and a cup of pineapple juice from the can.
Prepare a cupcake pan: Grease each well of a cupcake pan and add melted butter and brown sugar, spreading it around.
Add the cupcake batter: Chop the pineapple slices and add the pineapple chunks to the cupcake pan and then add a cherry to each. Divide the batter between the cupcake pan wells.
Bake the cupcakes: Bake until a toothpick inserted into the middle of a cupcake comes out clean. Let them cool on a parchment paper lined baking sheet.
Substitutions and Variations
Gluten-free option: If you want a gluten-free version, use a gluten-free cake mix.
Canned pineapple: Use fresh pineapple if you prefer. Just ensure you slice it into even slices first, then cut those pieces into 8 pieces to fit in the cupcake tins and avoid excess juice. Crushed pineapple would work too but wouldn’t look as pretty.
Cupcake batter: You can use a different flavor of cake mix or your favorite homemade cake recipe.
Serving Suggestions
Appetizers: Begin your meal with lentil soup or an antipasto farro salad.
Main dishes: Treat your taste buds to a loaded chorizo baked potato or teriyaki steak bites with hibachi fried rice.
Desserts: Finish up with these delicious pineapple upside down cupcakes.
How to Store Pineapple Cherry Cupcakes
Store: Refrigerate any leftover cupcakes in an airtight container or wrapped tightly with plastic wrap and eat within a few days.
Freeze: You can freeze these in an airtight container for up to 3 months. I recommend wrapping each one tightly in plastic wrap and then putting them in a Ziploc bag.
Thaw: Defrost them in the refrigerator overnight.
Top Tips
Pineapple juice: Dole sliced pineapple in juice had the full cup of pineapple juice needed for this recipe. If a different brand is used, you may need to add enough water to the reserved juice to bring the volume to 1 cup.
Cupcake rising: The cupcakes are filled almost to the top of each cupcake, which is natural. There may be a slight rise during the baking process, but once cooked and resting for 10 minutes out of the oven (before inverting out onto a tray), the cupcakes will re-settle down slightly.
Topping options: Fresh whipped cream and/or a stemmed maraschino cherry would make a great topping. You could also dust each cupcake with some powdered sugar.
Pineapple Upside Down Cupcake FAQs
These cupcakes can be made a day ahead. Store them in an airtight container in the refrigerator and bring them to room temperature before serving.
Whichever you prefer – these cupcakes are delicious served either way.
Not for this recipe. Cupcake or muffin liners aren’t recommended, as the caramelized topping might stick to the paper. Grease the cake cups or muffin cups instead.
Cake Mix Pineapple Upside Down Cupcakes Recipe
Pineapple Upside Down Cupcakes
Equipment
- 2 Cupcake Pan 12-Cup
- Can Opener Optional
- Sieve Optional for Sifting Powdered Sugar
Ingredients
- 1 yellow cake mix, 15-ounce box, or pineapple cake mix
- 3 eggs
- ⅓ Cup vegetable oil
- ½ Cup butter, melted
- 1½ Cups light brown sugar
- 24 maraschino cherries, stems removed
- 1 Can pineapple slices, 20-Ounce can, reserving the juice
- 1 Cup pineapple juice, reserved juice from the can of sliced pineapple
Optional Toppings:
- whipped cream
- powdered sugar
- maraschino cherries, on the stem
Instructions
- Preheat the oven to 350°F.
- Generously spray each well of the cupcake pan with cooking spray or use shortening or oil.
- Cut each slice of pineapple into eight pieces each slice. This is easiest if you cut each slice in half, then cut those halves in half, and then finally each quarter is cut in half.
- In a mixing bowl, combine the cake mix, eggs, oil, and 1 cup of pineapple juice and mix well to combine.
- Pour 1 teaspoon of the melted butter into each well of the cupcake pan, then sprinkle 2 teaspoons of the brown sugar into each well. Spread the brown sugar around the bottom of the cupcake well.
- Press 3 pieces of cut pineapple slices and one stemless cherry in the center. The pineapple pieces might press out slightly.
- Scoop 3 tablespoons of the batter into each cupcake well until full.
- Gently tap the cupcake pan on the counter to release any air bubbles.
- Bake on the center rack for 18 to 20 minutes or until a toothpick inserted in the center comes out clean. If baking 2 trays at a time, rotate the cupcakes 10 minutes into the baking so each one bakes evenly.
- Let it cool for 10 minutes, then carefully turn them out onto a parchment-lined baking sheet.
- Allow the cupcakes to cool to room temperature, then serve dusted with powdered sugar or paired with fresh whipped cream.
Notes
Cupcake rising: The cupcakes are filled almost to the top of each cupcake, which is natural. There may be a slight rise during the baking process, but once cooked and resting for 10 minutes out of the oven (before inverting out onto a tray), the cupcakes will re-settle down slightly.
Topping options: Fresh whipped cream and/or a stemmed maraschino cherry would make a great topping. You could also dust each cupcake with some powdered sugar.
Nutrition
These delicious pineapple upside down cupcakes are so easy to make and they’re wonderfully moist and delicious with a pineapple and cherry topping. If you enjoy regular upside down cake, try this tasty twist with individual servings. Once you try these, you’ll definitely want to make them again and again.
Other Cupcake Recipes to Try
Bella Bucchiotti
Bella Bucchiotti is a Canadian-based syndicated food, travel, and lifestyle writer, photographer, and creator at xoxoBella. She founded xoxoBella in 2015, where she shares her love for food, dogs, sustainability, fitness, crafts, outdoor adventures, travel, and philanthropy to encourage others to run the extra mile, try new recipes, visit unfamiliar places, and stand for a cause. Bella creates stress-free and family-friendly recipes for weeknight dinners and festive feasts.
