Pineapple Upside-Down Cupcakes

Here’s a fun-sized twist on a classic dessert — Pineapple Upside-Down Cupcakes! These individual treats are soft, buttery, and caramelized with juicy pineapple and cherries. Perfect for parties or easy portion control!

Ingredients (Makes 10–12 cupcakes)

 Topping:

1/3 cup brown sugar

2 tbsp melted butter

6 pineapple rings (cut in halves or quarters)

6 maraschino cherries (halved)

 Cake Batter:

1/2 cup granulated sugar

1/4 cup softened butter

1 egg

1/2 tsp vanilla extract

1 cup all-purpose flour

1 1/2 tsp baking powder

1/4 cup milk

1/4 cup pineapple juice (from can)

Instructions

Prepare the Pan:

Grease a muffin tin or silicone cupcake molds that fit your air fryer or oven.

Make the Topping:

In each cup, add:

1 tsp melted butter

1 tsp brown sugar

Place a small pineapple piece & cherry half on top

Mix the Batter:

Cream butter and sugar until fluffy.

Beat in egg and vanilla.

In a separate bowl, mix flour and baking powder.

Alternate adding flour mixture, milk, and pineapple juice to wet ingredients. Mix until smooth.

Assemble:

Spoon batter over the pineapple/cherry (fill each 2/3 full).

Bake:

Bake until golden and a toothpick comes out clean.

Cool & Flip:

Let cool 5 minutes, then carefully invert onto a plate while warm.

Tips & Tricks

Don’t overfill — they rise!

Use pineapple tidbits for more fruit in each bite.

Silicone molds work best in air fryers (easy release).

Add a touch of cinnamon to the batter for warmth.

Nutrition Estimate (Per cupcake)

Calories: ~180

Fat: 7g

Carbs: 28g

Sugar: 17g

Protein: 2g

Why You’ll Love Them

Mini versions of a retro favorite

Sweet pineapple and cherry topping

Moist vanilla cake base

Great for air fryer or oven!