Pineapple Upside Down Cupcakes


cooking spray

½ cup butter, melted

1 ½ cups brown sugar

24 maraschino cherries

1 (20 ounce) can crushed pineapple

1 (18.25 ounce) package pineapple cake mix (such as Duncan Hines® Pineapple Supreme)

3 eggs

1 ⅓ cups pineapple juice

⅓ cup vegetable oil

1 tablespoon confectioners’ sugar for dusting, or as needed


Step 1
Move an oven rack into the middle of the oven. Preheat oven to 350 degrees F (175 degrees C).

Step 2
Spray 24 muffin cups with cooking spray.

Step 3
Line a work surface with waxed paper.

Step 4
Spoon 1 teaspoon melted butter into the bottom of each sprayed muffin cup.

Step 5
Spoon 1 tablespoon brown sugar in each muffin cup.

Step 6
Press a maraschino cherry into the center of the brown sugar in each muffin cup.

Step 7
Spoon a heaping tablespoon of crushed pineapple over the cherry and compact it with the back of a spoon into an even layer.

Step 8
Mix pineapple cake mix, eggs, pineapple juice, and vegetable oil in a large bowl with electric mixer on low speed until moistened, about 30 seconds. Turn mixer speed to medium and mix for 2 minutes.

Step 9
Pour pineapple cake batter into the muffin cups, filling them to the top; do not overfill.

Step 10
Bake in the preheated oven until a toothpick inserted into the center of a cupcake comes out clean, about 20 minutes.

Step 11
Allow cupcakes to cool at least 5 minutes before inverting muffin cups onto the waxed paper to release. Serve with pineapple and cherry sides up. Sprinkle cupcakes lightly with confectioners’ sugar.