Introduction

Pineapple Upside Down Cupcakes are a delightful twist on the classic dessert, perfect for individual servings. These moist cupcakes feature caramelized pineapple and brown sugar on the bottom, which becomes a beautiful topping when flipped. They’re finished with a dollop of sweetened whipped cream and a maraschino cherry for a tropical treat.

A small round cake with a golden brown base topped with a layer of yellow pineapple chunks, then a swirl of white whipped cream, and a bright red cherry with a long stem on top. Another red cherry sits on the white plate beside the cake, and a silver fork rests on the left side of the plate. The plate is on a white marbled surface with two similar plates and cakes blurred in the background. photo taken with an iphone --ar 4:5 --v 7

Ingredients

1 (20 oz) can pineapple chunks in pineapple juice
1 (8 oz) can pineapple chunks in pineapple juice
1/3 cup (2.7 oz) packed light brown sugar
1/3 cup (2.6 oz) unsalted butter
1 cup (5 oz) all-purpose flour
3/4 cup (5.6 oz) granulated sugar
1/2 tsp baking powder
1/4 tsp salt
1/4 cup (2 oz) unsalted butter, softened
1/2 cup (4 oz) pineapple juice (from pineapple chunk can)
1 large egg
1/2 tsp vanilla extract
3/4 cup heavy cream
2 Tbsp granulated sugar
12 maraschino cherries

Instructions

Step 1: Preheat oven to 350 degrees F. Spray 12 muffin cups well with non-stick cooking spray.
Step 2: Drain both cans of pineapple chunks while reserving 1/2 cup of the juice for the batter. Place pineapple chunks on several layers of paper towels to drain thoroughly. Melt 1/3 cup butter in a microwave-safe bowl, then stir in the brown sugar until combined.
Step 3: Divide the butter and sugar mixture evenly among muffin cups, about 2 teaspoons each. Arrange about 5 pineapple chunks on top of the sugar mixture in each cup. It’s okay if pineapple chunks vary in size and shape; just try to fit about 5 pieces per cup.
Step 4: In the bowl of an electric stand mixer, whisk together the flour, 3/4 cup sugar, baking powder, and salt.
Step 5: Using the paddle attachment, add the softened 1/4 cup butter and reserved pineapple juice to the dry ingredients. Mix on medium speed until smooth, about 1 to 2 minutes. Occasionally scrape the bowl if needed.
Step 6: Add the egg and vanilla extract, mixing until well combined. Then, evenly divide the batter among the muffin cups, carefully layering it over the pineapple slices.
Step 7: Bake in the preheated oven until a toothpick inserted into the center of a cupcake comes out clean, about 23 to 26 minutes. Let cool for 5 minutes in the pan, then run a sharp knife around each cupcake to loosen.
Step 8: Place a wire cooling rack over the muffin pan and carefully flip the pan to invert the cupcakes onto the rack. Let them cool completely before adding the whipped cream.
Step 9: To make the sweetened whipped cream, whip the heavy cream on high speed until soft peaks form. Add 2 tablespoons of granulated sugar and continue whipping until stiff peaks form.
Step 10: Pipe or dollop the whipped cream over each cooled cupcake and top with a maraschino cherry before serving.

Tips & Variations

For a more intense pineapple flavor, soak the pineapple chunks in a splash of rum before arranging them in the cups.
If you prefer, substitute maraschino cherries with fresh cherries or pineapple chunks for garnish.
Use fresh pineapple chunks when in season for a fresher, more vibrant taste.
If you don’t have a stand mixer, a hand mixer or vigorous whisking will also work to make the batter smooth.

Storage

Store leftover cupcakes in an airtight container in the refrigerator for up to 3 days. Add the whipped cream topping just before serving to keep it fresh and fluffy. To reheat, warm cupcakes briefly in the microwave for about 10 seconds, but avoid reheating if topped with whipped cream.

How to Serve

A group of small cakes arranged in rows on a black cooling rack is shown, each cake has three layers: the base is a light brown sponge cake with a moist texture, topped with a glossy yellow fruit layer, likely pineapple, followed by a swirl of white whipped cream on top, finished with a bright red cherry with stem placed neatly at the peak of the whipped cream. The scene is set on a white marbled surface with a wooden edge partially visible at the bottom. photo taken with an iphone --ar 4:5 --v 7

Serve this delicious recipe with your favorite sides.

FAQs

Can I use fresh pineapple instead of canned?

Yes, fresh pineapple chunks work well. Be sure to drain them well to avoid excess moisture in the cupcakes.

Can these cupcakes be made ahead of time?

You can prepare and bake the cupcakes ahead, then store them refrigerated. Add whipped cream and cherries just before serving for best texture and presentation.

Pineapple Upside Down Cupcakes Recipe

Print Recipe

★★★★★

4.8 from 108 reviews

These Pineapple Upside Down Cupcakes offer a delightful twist on the classic pineapple upside-down cake. Individual-sized and topped with sweet pineapple chunks caramelized in brown sugar and butter, these cupcakes are finished with a cloud of whipped cream and a maraschino cherry for a perfect party treat or a tropical-inspired dessert.

Author: Elias
Prep Time: 15 minutes
Cook Time: 25 minutes
Total Time: 40 minutes
Yield: 12 cupcakes 1x
Category: Dessert
Method: Baking
Cuisine: American

Ingredients

Scale

Cake and Topping

1 (20 oz) can pineapple chunks in pineapple juice
1 (8 oz) can pineapple chunks in pineapple juice
1/3 cup (2.7 oz) packed light brown sugar
1/3 cup (2.6 oz) unsalted butter
1 cup (5 oz) all-purpose flour
3/4 cup (5.6 oz) granulated sugar
1/2 tsp baking powder
1/4 tsp salt
1/4 cup (2 oz) unsalted butter, softened
1/2 cup (4 oz) pineapple juice (reserved from canned pineapple)
1 large egg
1/2 tsp vanilla extract
12 maraschino cherries

Sweetened Whipped Cream

3/4 cup heavy cream
2 Tbsp granulated sugar

Instructions

Preheat Oven and Prepare Muffin Pan: Preheat your oven to 350°F (175°C). Spray 12 muffin cups generously with non-stick cooking spray to prevent sticking.
Drain Pineapple and Prepare Caramel Mixture: Drain both cans of pineapple chunks, reserving 1/2 cup of the juice for the batter. Place the pineapple chunks on several layers of paper towels to drain thoroughly. Melt 1/3 cup unsalted butter in a microwave-safe bowl, then stir in the packed light brown sugar until fully combined.
Assemble Pineapple Topping in Muffin Cups: Divide the brown sugar and butter mixture evenly among the 12 muffin wells, placing about 2 teaspoons in each. Arrange approximately 5 pineapple chunks on top of the sugar mixture in each cup, trying to create a tight arrangement for a floral effect. You might not need all the pineapple chunks depending on their size.
Mix Dry Ingredients for Batter: In a stand mixer bowl, whisk together the all-purpose flour, granulated sugar, baking powder, and salt until well combined.
Add Wet Ingredients to Batter: Using the paddle attachment, add the 1/4 cup softened butter and 1/2 cup reserved pineapple juice to the dry ingredients. Mix at medium speed until the batter is smooth, about 1 to 2 minutes. Stop occasionally to scrape down the sides and bottom of the bowl for thorough mixing.
Incorporate Egg and Vanilla: Mix in the large egg and vanilla extract until well combined and smooth.
Fill Muffin Cups and Bake: Evenly divide the batter over the pineapple layers in the muffin cups, covering them completely. Bake in the preheated oven for 23 to 26 minutes, or until a toothpick inserted into the center of a cupcake comes out clean.
Cool and Invert Cupcakes: Remove the cupcakes from the oven and allow them to cool for 5 minutes in the pan. Run a sharp knife around the edges to loosen them. Place a wire cooling rack on top of the muffin pan, then carefully flip the pan and rack together to invert the cupcakes onto the rack. Let them cool completely.
Prepare Sweetened Whipped Cream: In a mixing bowl using an electric hand mixer (or stand mixer with whisk attachment), whip the heavy cream on high speed until soft peaks form. Gradually add 2 tablespoons of granulated sugar and continue whipping until stiff peaks form.
Pipe Whipped Cream and Garnish: Just before serving, pipe or dollop the sweetened whipped cream over each cooled cupcake and top each with a maraschino cherry for a colorful, classic finish.

Notes

Draining the pineapple chunks well is essential to prevent the topping from becoming soggy.
You can adjust the amount of brown sugar and butter mixture on top depending on your sweetness preference.
If pineapple chunks are large, fewer per cupcake may be best to fit the pan.
Make sure to let cupcakes cool completely before adding whipped cream to prevent it from melting.
These cupcakes can be stored in an airtight container in the refrigerator for up to 3 days.

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