Pineapple Upside Down Cupcakes

Perfect for parties, these Pineapple Upside Down Cupcakes deliver retro charm and modern convenience. Each cupcake features a caramelized pineapple ring with a cherry center and moist vanilla cake.

5 from 1 vote

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Course: Dessert

Cuisine: American

Keyword: Best pineapple upside down cupcakes, Old fashioned pineapple upside down cupcakes, Pineapple upside down cake, Pineapple Upside Down Cupcakes, Pineapple upside down cupcakes in liners, Pineapple upside down cupcakes with cake mix

Prep Time: 20

Cook Time: 20

Cooling Time: 10

Total Time: 50

Servings: cupcakes

Calories: 220kcal

Cost: $10

Equipment

12-cup muffin tin (Well-greased)
Electric mixer (Hand or stand mixer)
Large mixing bowl
Wire cooling rack (For flipping and cooling cupcakes)
Knife (For loosening cupcake edges)
Can opener (For canned pineapple)

Ingredients

For the Caramelized Topping:

6 tablespoon Unsalted butter - Melted
⅔ cup Brown sugar - Light or dark
6 Pineapple rings - Cut in halves to fit muffin cups
12 Maraschino cherries - Drained

For the Cupcake Batter:

1½ cups All-purpose flour
¾ cup Granulated sugar
½ cup Unsalted butter - Softened
2 Large eggs - Room temperature
1½ teaspoon Baking powder
¼ teaspoon Salt
1 teaspoon Vanilla extract
½ cup Milk - Whole preferred

Optional Flavor Boosters:

2 tablespoon Pineapple juice - Replace part of milk
½ teaspoon Coconut extract - Adds tropical flair
½ teaspoon Rum extract - For adult flavor
1 teaspoon Lemon zest - Brightens flavor

Instructions

Preheat oven to 350°F and grease a 12-cup muffin tin thoroughly.
Mix melted butter with brown sugar and place in muffin cups. Add pineapple rings and cherries.
Cream butter and sugar, add eggs and vanilla, then mix in dry ingredients alternately with milk.
Spoon the batter over the fruit in muffin cups, filling each about ⅔ full.
Bake for 18–22 minutes until golden and a toothpick comes out clean.
Cool 5 minutes, run a knife around edges, flip onto a rack, and let sit 2 minutes before lifting.

Notes

Nutrition information is automatically calculated and should be considered an approximation. Actual values may vary based on specific ingredients used and portion sizes.

Nutrition