Pineapple Cupcakes

A pineapple upside down cupcake on top of three plates stacked on the table with a few more cupcakes on the edges and a jar of milk in the background.

4.85 from 19 votes

These aren't just any pineapple cupcakes. These are pineapple cupcakes with a layer of fruit on the bottom and cream cheese pineapple frosting on top! Finished off with a dehydrated pineapple flower.

Prep Time10

Cook Time18

Cooling30

Total Time58

Course: Dessert

Cuisine: Southern

Servings: cupcakes

Calories: 316kcal

Author: Jocelyn Delk Adams

Equipment

Ingredients

Cake

⅓ cup unsalted butter room temperature
⅔ cup vegetable oil
1 ½ cup granulated sugar
3 large eggs room temperature
2 ¾ cups all-purpose flour
1 ½ teaspoon baking powder
½ teaspoon baking soda
1 teaspoon fine sea salt
1 ¼ cup sour cream room temperature
⅓ cup whole milk or another milk of your choice
2 teaspoons vanilla extract
1 teaspoon rum or pineapple extract
½ cup unsalted butter melted
¾ cup brown sugar
8.25 ounces crushed pineapple drained (save juice)

Frosting

½ cup unsalted butter softened
4 ounces cream cheese softened
2 cups confectioner’s sugar
2 tablespoons crushed pineapple
1 teaspoon vanilla extract
1-2 tablespoons pineapple juice

Instructions

For The Cupcakes

Preheat oven to 350F. Place rack to middle position. Place cupcake liners in two 12-cup muffin pans. (You will need four more so you can wait until a batch of cupcakes bake before lining with the remaining ones.)
In a stand mixer with a paddle attachment, mix butter, oil, and sugar on high speed, until very pale and fluffy, about 4minutes. Meanwhile, sift flour, baking powder, soda, and salt in a large bowl.
Reduce speed to medium and add eggs, one at a time combining well after each addition, scraping down the sides of the bowl as needed.
Reduce speed to low and slowly add sifted dry ingredients. Mix until just combined. DO NOT OVERMIX.
Lastly, add sour cream, milk, vanilla, and rum. Scrape down sides of bowl and mix until just combined. Turn off mixer.
Spoon 1 teaspoon of melted butter into the bottom of each liner. Top butter with 1 teaspoon of brown sugar. Finally spoon 1 teaspoon of crushed pineapple over brown sugar and spread out on bottom of liner.
Using an ice cream scoop, add cake batter to each liner over the pineapple. The liner should be three-quarters full.
Bake until light golden brown, a toothpick inserted into the center of the cupcakes come out clean, about 18-20 minutes.
Allow cupcakes to cool in the pan for 10 minutes, then remove from the pan and place them on a cooling rack to cool completely, about 20 minutes.

For The Pineapple Frosting

While cupcakes cool, place butter, cream cheese, and confectioner’s sugar in bowl of a stand mixer fitted with the paddle. Mix on high for 2 minutes.
Next, add crushed pineapple, vanilla extract, and pineapple juice in small amounts to frosting, making sure the frosting isn’t too loose. Mix until thickened and fluffy.
Frost each cupcake once it’s completely cool and enjoy!

Notes

Don't overmix. I can't overstate the importance of not mixing too much. Mixing causes the gluten to form too much and leads to a tough cake.

Use an ice cream scoop. The cleanest and easiest way to transfer the cake batter to the cupcake pan is by using an ice cream scoop. If you don't have one, use a measuring cup instead.

Allow the cupcakes to cool completely before adding the frosting. If they are too hot the frosting may melt.

Use cupcake liners. This will keep the pineapple mixture from sticking but also keep it connected to the cupcake so you enjoy the sugary, sweetness of pineapple in each bite.

Nutrition