Pineapple Upside-Down Cupcakes

published May 22, 2022
Pineapple Upside Down Cupcakes Recipe

This cuter cupcake form of the classic cake is an individual portion that's easy to serve for a dinner party or transport to a summer potluck.


Prep30 minutes

Cook33 minutes to 42 minutes

Jump to Recipe
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pineapple upside down cupcakes  on a cooling rack.
Credit: Shilpa Uskokovic

Pineapple upside-down cake is an iconic American dessert that peaked in popularity in the 1950s and ’60s. We have seen other upside-down versions made with “trendier fruits” throughout the decades, like pears, plums, or blood oranges. Nothing could dethrone the appeal and love of the iconic pineapple with neon red maraschino cherries. This cuter cupcake form is an individual portion that’s easy to serve for a dinner party or transport to a summer potluck. 

Fresh vs. Canned Pineapple

After testing this recipe a few times with fresh pineapple, I can attest that the flavor was much brighter than its canned counterpart. But there are challenges with fresh pineapple, like cutting it up, which isn’t a delicate task. It is also rare to come across a pineapple that is ready to use and doesn’t require days of waiting for it to ripen. Because these cupcakes are supposed to be simple, I opted to use canned pineapple for a classic feel along with ease and consistency.

How to Keep Pineapple Upside Down Cupcakes from Sticking

I prefer to get the canned pineapple rings for easier dicing, as chunks are too big and require further dicing. Crushed pineapple might seem like a suitable substitution, but it is too small, can stick to the bottom of the pan, and, when cooked, lacks proper texture, creating a more jammy consistency.

Credit: Shilpa Uskokovic

How to Achieve the Best Pineapple Upside-Down Cupcakes

Considering we are making a cupcake version of this iconic cake, the baking time isn’t sufficiently long enough to cook the pineapple and create a compact fruit layer. That’s why we jumpstart the process by pre-cooking the pineapple in the oven, a process that also further caramelizes the dark brown sugar and butter for a more complex flavor.

Pineapple Upside Down Cupcakes Recipe

This cuter cupcake form of the classic cake is an individual portion that's easy to serve for a dinner party or transport to a summer potluck.

Prep time 30 minutes

Cook time 33 minutes to 42 minutes

Serves 12

Nutritional Info


  • Cooking spray

  • 14 tablespoons

    unsalted butter, divided

  • 1 (20-ounce) can

    pineapple slices in 100% pineapple juice

  • 2/3 cup

    packed dark brown sugar

  • 1/3 cup

    plus 2 tablespoons reserved pineapple juice from the canned pineapple, divided

  • 2 teaspoons

    kosher salt, divided

  • 2 1/2 cups

    sifted bleached cake flour

  • 2 teaspoons

    baking powder

  • 1 cup

    granulated sugar

  • 2

    large eggs

  • 1 tablespoon

    neutral oil, such as vegetable or canola

  • 1

    large lemon

  • 1 cup

    full-fat sour cream

  • 1 teaspoon

    vanilla bean paste

  • 1/4 teaspoon

    grated nutmeg

  • Serving options: whipped cream, ice cream, or maraschino cherries (preferably Luxardo)


Make the pineapple topping:

  1. Arrange a rack in the middle of the oven and heat the oven to 375°F. Coat the wells of a standard 12-well muffin pan with cooking spray.

  2. Cut 14 tablespoons unsalted butter into cubes. Place in a small microwave-safe bowl and microwave until melted, about 1 minute. Drain 1 (20-ounce) can pineapple slices, reserving the juice. Cut the pineapple into roughly 1/4-inch pieces (about 1 1/3 cups).

  3. Place 2/3 cup packed dark brown sugar, 7 tablespoons of the melted butter, 2 tablespoons of the pineapple juice, and 1 teaspoon of the kosher salt in a small bowl and stir until well combined. Spoon 1 tablespoon of the sugar mixture into each muffin well. Spoon 1 1/2 tablespoons of the diced pineapple into each well; pressing down with the back of a spoon to ensure the fruit is tightly packed.

  4. Bake until sugar bubbles around the fruit, darkens in color slightly, and the pineapple begins to becomes translucent, 15 to 20 minutes. Remove from the oven and set aside to cool while you make the cake batter.

Make the cupcakes:

  1. Line a rimmed baking sheet with parchment paper or aluminum foil.

  2. Place 2 1/2 cups sifted cake flour and 2 teaspoons baking powder in a medium bowl and whisk until well combined.

  3. Place the remaining 7 tablespoons melted butter, remaining 1 teaspoon kosher salt, 1 cup granulated sugar, 2 large eggs, and 1 tablespoon vegetable oil in in a large bowl and whisk until creamy and well combined. Finely grate the zest of 1 large lemon into the bowl. Add 1 cup sour cream, 1/3 cup of the pineapple juice, 1 teaspoon vanilla bean paste, and 1/4 teaspoon grated nutmeg, and whisk until well combined.

  4. Add flour mixture to butter mixture and mix with a whisk just until it comes together and no large, dry streaks of flour remain. Switch to a rubber spatula and fold the batter a few times, scraping the sides and bottom of the bowl to ensure everything is well mixed. Using a 2-ounce cookie or ice cream scoop, scoop the batter into each muffin well to fill about 3/4 full. (If you have any leftover batter, you can bake off a few extra plain cupcakes or discard.)

  5. Place the muffin pan on the baking sheet. Bake until the cupcakes springs back when lightly pressed in the middle and a cake tester inserted in the center of one comes out clean, 18 to 22 minutes.

  6. Let the cupcakes cool in the pan for 10 minutes. Gently run a small offset spatula or butter knife around the edge of each cupcake to loosen. Remove the parchment or foil from the baking sheet. Invert the baking sheet over the muffin pan. Grasping the muffin pan and baking at the same time with kitchen towels or oven mitts to protect your hands, flip them over in one motion. Carefully lift the muffin pan away; if any pineapple remains stuck, just spoon it back onto the cupcake. Let the cupcakes cool for at least 15 minutes more before serving with whipped cream or ice cream and a cherry on top if desired.

Recipe Notes

Bleached cake flour substitute: If you can’t find bleached cake flour, you can substitute it with 2 1/4 cups sifted bleached all-purpose flour.

Storage: Leftovers can be refrigerated in an airtight container for up to 2 days.