Pineapple Upside Down Cupcakes

These pineapple upside down cupcakes are a tropical twist on the classic dessert, made mini and easy to serve. They’re perfect for parties, gatherings, or whenever you want a fun, fruity treat!

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Course: Cupcakes, Dessert

Cuisine: American, Tropical-Inspired

Prep Time: 15

Cook Time: 20

Cooling Time: 10

Total Time: 45

Servings: cupcakes

Calories: 230kcal

Cost: $8–$10 (depends on ingredients used)

Equipment

1 12-cup muffin tin Light-colored preferred
2 Mixing bowls One large, one medium
1 Whisk or mixer Manual or electric
1 set Measuring cups/spoons For precise ingredient measurement
1 Rubber spatula For folding and scraping batter
1 Wire cooling rack Optional, for cooling
1 Knife To trim pineapple if needed
1 Serving plate For flipping cupcakes after baking

Ingredients

12 rings Fresh pineapple Pat dry + optional cornstarch dusting
12 Maraschino cherries Whole, patted dry
½ cup Brown sugar Packed
¼ cup Butter Melted
1 ¼ cups All-purpose flour
¾ cup Granulated sugar
2 Eggs Room temperature
1 teaspoon Vanilla extract
1 ½ teaspoon Baking powder
½ teaspoon Salt
½ cup Whole milk Room temperature
¼ cup Vegetable oil

Instructions

Preheat oven to 350°F and grease muffin tin.
Combine melted butter and brown sugar.
Divide topping into muffin cups, add pineapple and cherry.
Whisk flour, sugar, baking powder, and salt.
Mix eggs, milk, oil, and vanilla separately.
Combine wet and dry mixtures without overmixing.
Spoon batter over pineapple in cups.
Bake 18–20 minutes until golden and toothpick comes out clean.
Cool 5 minutes, run knife around edges, flip onto plate.
Let cool completely before serving.

Notes

For best results, ensure fruit is patted dry to avoid sogginess. Light-colored muffin tins help prevent over-browning of the caramelized topping.

Nutrition