Caramelized Pineapple Upside-Down Cupcakes Recipe

These Pineapple Coconut Upside Down Cupcakes take a beloved classic and transform it into a tropical, caramel-scented treat. Each cupcake is crowned with a caramelized pineapple chunk and made from a moist, coconut-infused cake that balances sweet and tart flavors for an irresistible bite.

Shredded coconut and coconut oil give the batter a gentle, nutty aroma while pineapple juice replaces plain water to boost the tropical profile. Brown sugar melts onto the pineapple as it bakes, rounding out the tanginess and adding a glossy, sticky finish. If you want a simple, show-stopping dessert for gatherings or an easy weekend bake, these cupcakes are a great pick.

Instead of a single-layer sheet cake, making this as individual cupcakes gives each serving its own caramelized pineapple centerpiece. Cupcakes are easier to portion and transport, and the caramelized topping clings to each mini cake so you don’t have to worry about messy slices. These are ideal warm from the oven or chilled with a dollop of whipped cream.

Pineapple Coconut Upside Down Cupcakes – What You’ll Need

• Unsweetened shredded coconut: Adds texture and a clean coconut flavor throughout the cake.
• Coconut oil: Replaces butter for a subtle tropical richness in the batter.
• Almond extract: A small amount enhances the nutty coconut notes without tasting overly almond-y.
• Pineapple juice: Use pineapple juice instead of water to infuse the batter with extra pineapple flavor.
• Eggs: Provide structure and moisture to the cupcakes.
• Brown sugar: Coats the pineapple chunks to caramelize during baking and create a sticky topping.
• Pineapple chunks: Canned pineapple chunks are recommended for a soft texture that bakes well.

What kind of pineapple should I use?

For convenience and consistent texture, canned pineapple chunks work best for this recipe. Canned fruit is softer and caramelizes well in the muffin tin. One 20-ounce can of pineapple chunks provides both the juice and the pieces needed for the recipe.

Where’s the maraschino cherry?

This version uses pineapple chunks instead of rings, so maraschino cherries are optional. If you prefer the classic look, you can swap in pineapple rings and add a cherry in the center of each ring before baking.

How to Make Pineapple Upside Down Cupcakes

1. Preheat & prepare: Preheat the oven to 350°F (175°C). Spray a 12-cup muffin tin with cooking spray or grease it well and set aside.
2. Mix dry ingredients: In a bowl whisk together the dry ingredients until evenly combined.
3. Cream oil and sugar: In a separate large bowl, beat the coconut oil with an electric mixer until smooth. Add the granulated sugar and almond extract and beat until light and fluffy.
4. Add pineapple juice & eggs: Slowly add pineapple juice while mixing on low. The mixture may look slightly separated as coconut oil can congeal—this is normal. Add eggs one at a time, mixing just until combined.
5. Combine wet & dry: Gradually add the dry ingredients to the wet mixture, scraping the bowl as needed. Mix until just incorporated; do not overmix.
6. Assemble: Toss pineapple chunks with brown sugar so they are coated. Place about 1 tablespoon of the sugared pineapple in the bottom of each muffin cup. Spoon about 3 heaping tablespoons of batter over each portion of pineapple.
7. Bake: Bake for 18–22 minutes, or until a toothpick inserted into the center of a cupcake comes out clean.
8. Cool & flip: Let the cupcakes cool in the pan for about 5 minutes, then invert onto a baking sheet or platter so the pineapple is on top. Serve warm or at room temperature.

Here’s a tip!

Resist overmixing the batter. Overmixing develops gluten and can lead to denser, drier cupcakes. Stir just until the ingredients are combined for a tender crumb.

Storing Pineapple Coconut Upside Down Cupcakes

Store these cupcakes in an airtight container in the refrigerator to preserve their texture and moisture. They will keep well for up to 3 days. Reheat briefly before serving if you prefer them warm.

Pairings and Serving Suggestions

These cupcakes are delicious on their own, but a scoop of vanilla ice cream or a dollop of whipped cream makes them feel extra special. For a summer dessert, serve warm with chilled fruit-based ice cream or a light whipped topping.

The bright, fruity flavor also pairs nicely with lightly sweet wines like Moscato or a semi-dry Riesling, and a sparkling wine can add a festive finish when serving these cupcakes at a gathering.

Pineapple Upside Down Cupcakes – Recipe Details

Author: Emily Richter

Yield: 12 cupcakes  |  Prep: 20 mins  |  Cook: 22 mins  |  Total: 42 mins

Ingredients

• Dry
  • 1.5 cups all-purpose flour
  • 1/3 cup unsweetened shredded coconut
  • 2 teaspoons baking powder
  • 1/2 teaspoon kosher salt
• Wet
  • 1/3 cup coconut oil
  • 3/4 cup granulated sugar
  • 1 teaspoon almond extract
  • 3/4 cup pineapple juice
  • 2 large eggs
• Topping
  • 2 tablespoons brown sugar
  • 1 cup canned pineapple chunks, divided

Instructions (short)

• Preheat oven to 350°F and prepare a 12-cup muffin tin.
• Whisk dry ingredients together. Beat coconut oil, sugar, and almond extract until fluffy. Add pineapple juice slowly, then eggs one at a time.
• Fold in dry ingredients until just combined. Toss pineapple chunks with brown sugar and place in muffin wells. Fill with batter and bake 18–22 minutes.
• Cool 5 minutes in the pan, invert, and serve.

Tips & Notes

• Caramelization will vary depending on your pan and oven—nonstick or well-greased pans work best for easy release.
• Canned pineapple is recommended for consistent softness and moisture.
• One 20 oz. can of pineapple chunks typically provides the juice and pieces required for this recipe.

Nutrition (approximate per cupcake)

Calories: 209 kcal  |  Carbohydrates: 32 g  |  Protein: 3 g  |  Fat: 9 g  |  Fiber: 1 g  |  Sugar: 18 g