Pineapple upside-down cupcakes are the classic cake in single servings: a butter and brown sugar base, crushed pineapple and a cherry in each muffin cup, and a pineapple cake mix batter baked on top. Flip the pan and every cupcake comes out with its own glossy topping.
How to make pineapple upside-down cupcakes with cake mix: Put 1 teaspoon of melted butter, 1 tablespoon of brown sugar, a cherry and a spoonful of drained crushed pineapple in each of 24 muffin cups. Beat the cake mix with the pineapple juice, eggs and oil, fill the cups 2/3 full, bake at 350°F for about 20 minutes, rest 5 minutes and turn them out.
Why You’ll Love Them
- Cake mix shortcut: a box of pineapple cake mix does the work, and the juice from the can replaces the water.
- Makes 24: one batch fills two standard muffin pans.
- Ready in 40 minutes: 20 minutes to build and 20 minutes to bake.
- No slicing: each cupcake has its own pineapple and cherry, so every serving looks the same.
Ingredient Notes
Butter and brown sugar: Half a cup of melted butter and 1 1/2 cups of brown sugar make the sticky caramel base. That is 1 teaspoon of butter and 1 tablespoon of sugar per cup.
Crushed pineapple: One 20-ounce can. Drain it well over a measuring cup and keep the juice. Wet pineapple makes soggy bottoms.
Pineapple juice: The batter takes 1 1/3 cups. A can of crushed pineapple rarely gives that much, so top up the reserved juice with water or bottled pineapple juice.
Cake mix: The recipe was written for an 18.25-ounce pineapple cake mix, such as Duncan Hines Pineapple Supreme. Many boxes are smaller now. If yours is, use the eggs, oil and liquid printed on your box, and use the pineapple juice for the liquid. Yellow or vanilla cake mix works too.
Maraschino cherries: One per cupcake, 24 in all. Pat them dry so the red juice does not bleed into the topping.
Eggs and oil: Three large eggs and 1/3 cup of vegetable oil for the full-size mix.
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Ingredients
- 1/2 cup melted butter, for the topping
- 1 1/2 cups brown sugar, for the topping
- 24 maraschino cherries
- 1 can (20 oz) crushed pineapple, well drained
- 1 package (18.25 oz) pineapple cake mix
- 1 1/3 cups pineapple juice, reserved from the can and topped up with water
- 3 large eggs
- 1/3 cup vegetable oil
- 1 tbsp confectioners’ sugar, optional, for dusting
How to Make Pineapple Upside-Down Cupcakes
1. Prepare the pans. Heat the oven to 350°F (175°C). Spray 24 standard muffin cups well with cooking spray. Do not use paper liners, or the topping cannot turn out.
2. Build the topping. Put 1 teaspoon of melted butter in each cup, then 1 tablespoon of brown sugar. Press a cherry into the center and spoon a heaping tablespoon of crushed pineapple over it. Press it down gently into an even layer.
3. Make the batter. In a large bowl, combine the cake mix, pineapple juice, eggs and oil. Beat on low for 30 seconds, then on medium for 2 minutes until smooth.
4. Fill the cups. Pour the batter over the pineapple, filling each cup about 2/3 full.
5. Bake. Bake for about 20 minutes, until a toothpick in the center of a cupcake comes out clean.
6. Turn them out. Let the cupcakes rest in the pan for 5 minutes. Run a knife around each one, set a baking sheet lined with wax paper on top of the pan and flip it over. Lift the pan off.
7. Finish. Dust with confectioners’ sugar if you like, and serve warm or at room temperature.
How to Get a Clean Flip
The 5-minute rest matters. Turn the cupcakes out too soon and they are soft enough to tear. Wait too long and the brown sugar sets like glue in the pan.
If some topping sticks, scrape it out with a small spoon while it is still warm and press it back on the cupcake. Nobody will notice.
Grease the pan well, right up the sides. The batter rises above the topping, and a dry rim is where most cupcakes catch.
Tips for Success
Why are my cupcakes soggy on the bottom?
The pineapple was not drained enough. Press it in a sieve before you spoon it into the cups.
Why did the batter overflow?
The cups were too full. Filling them 2/3 full leaves room for the cake to rise.
Why are they dry?
They baked too long. Start checking a few minutes early, because ovens and pans vary.
Variations
- Pina colada style: stir 1/2 cup of shredded coconut into the batter, or sprinkle toasted coconut over the tops.
- Mini cupcakes: use a mini muffin pan, scale the topping down and bake for less time, checking early.
- Rum topping: stir 1 tablespoon of dark rum into the melted butter before it goes in the cups.
- Pineapple rings: cut canned rings into quarters and use a piece in place of the crushed pineapple.
If you enjoy individual pineapple treats, Pineapple Soft Serve is piped into frozen cups and makes four servings.
Storage & Reheating
Keep leftovers in an airtight container in the refrigerator for up to 3 days. To freeze, wrap each cupcake and keep it in a freezer container for up to 3 months, then thaw in the refrigerator. Warm a cupcake in the microwave for about 20 seconds, or in a 350°F oven for about 5 minutes.
What to Serve With Them
Serve them warm with vanilla ice cream or whipped cream. If you want the full-size version, try our pineapple upside-down cake or the pecan upside-down cake. For more pineapple desserts, there is pineapple coconut surprise cake, Hawaiian pineapple coconut fluff, no-bake pineapple cream dessert and a warm pineapple bake.
Frequently Asked Questions
Can I use a box of Pillsbury cake mix?
Yes. Any pineapple, yellow or vanilla cake mix works. Follow the eggs and oil on that box and use pineapple juice in place of the water.
What kind of cake mix is best for pineapple upside-down cupcakes?
Pineapple cake mix gives the most pineapple flavor. Yellow cake mix is the next best choice, because its buttery flavor suits the brown sugar topping.
Should I change the box recipe?
Only the liquid. Swap the water for the juice from the can, topped up with water or bottled juice if you are short. Keep the eggs and oil the same.
Can I use cupcake liners?
No. The topping bakes into the bottom of the cup and needs to turn out onto the plate. Liners hold it in and make the flip impossible.
Pineapple Upside-Down Cupcakes with Cake Mix at a Glance
These cupcakes use a box of pineapple cake mix, so they are quick to make. The recipe makes 24 cupcakes in about 40 minutes.
- Bottom layer: melted butter, brown sugar, crushed pineapple and a maraschino cherry in each cup.
- Batter: pineapple cake mix with the reserved pineapple juice, eggs and vegetable oil.
- Finish: cool 5 minutes, flip them out and dust with confectioners’ sugar.
Final Notes
Drain the pineapple well, grease the pan right up the sides and flip after 5 minutes. If you have a question or make them, tell me how they turned out in the comments.
Pineapple Upside-Down Cupcakes
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Ingredients
- 1/2 cup melted butter for the topping
- 1 1/2 cups brown sugar for the topping
- 24 maraschino cherries
- 1 (20 oz) can crushed pineapple well-drained
- 1 (18.25 oz) package pineapple cake mix such as Duncan Hines® Pineapple Supreme
- 1 1/3 cups pineapple juice reserved from the crushed pineapple, topped up with water to 1 1/3 cups
- 3 large eggs
- 1/3 cup vegetable oil
- 1 tbsp confectioners' sugar optional, for dusting
Instructions
- Preheat your oven to 350°F (175°C) and spray 24 muffin cups with cooking spray.
- Place 1 teaspoon of melted butter into each muffin cup. Add 1 tablespoon of brown sugar on top of the butter, then press a maraschino cherry into the center. Spoon a heaping tablespoon of crushed pineapple over the cherry and brown sugar mixture, pressing down gently to create an even layer.
- In a large mixing bowl, combine the pineapple cake mix, reserved pineapple juice, eggs, and vegetable oil. Mix on low speed for 30 seconds, then increase speed to medium and beat for 2 minutes until smooth.
- Pour the prepared cake batter into the muffin cups, filling each about 2/3 full.
- Bake in the preheated oven for about 20 minutes, or until a toothpick inserted into the center comes out clean.
- Let the cupcakes cool in the pan for 5 minutes. Run a knife around the edges to loosen them, then carefully invert the muffin tin onto a baking sheet lined with wax paper.
- For an extra touch of sweetness, dust the tops of the cupcakes with confectioners' sugar before serving.
Notes
Nutrition
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Nutrition values are estimates based on the listed ingredients and serving count. Actual values vary with brands, cuts and portion sizes.
