Pineapple Slices – Fresh or canned, cut into small rings or chunks to fit inside each cupcake mold.
Maraschino Cherries – These sweet, colorful cherries add a traditional touch and a pop of color.
Brown Sugar – Creates the caramel-like glaze when combined with melted butter.
Butter – Adds richness and enhances the flavor of the brown sugar glaze.
Yellow Cake Mix or Vanilla Cake Batter – Using a cake mix speeds up the process, but you can make the batter from scratch if you prefer.
Eggs, Milk, and Oil (if using cake mix) – These ingredients provide structure, moisture, and fluffiness to the cupcakes.

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Before you start baking, gather your ingredients and prepare your workspace:

1 can (20 oz) pineapple rings, drained and cut into small pieces
½ cup maraschino cherries, drained
½ cup melted butter
¾ cup brown sugar
1 box yellow cake mix (plus ingredients required on the box, usually eggs, oil, and water)

To get the traditional “upside-down” effect, you’ll start with the toppings at the bottom of the cupcake tin:

Preheat your oven to 350°F (175°C) and grease a 12-cup muffin tin well to prevent sticking.
In each cupcake mold, add about 1 teaspoon of melted butter and 1 tablespoon of brown sugar, spreading it evenly.
Place a small pineapple piece in each cup, along with half of a maraschino cherry in the center.

You can either use a boxed cake mix or a homemade yellow cake batter for this recipe. Here’s how to prepare the batter:

Follow the instructions on the cake mix box, usually requiring eggs, oil, and water. Mix until smooth.
If making from scratch, beat together butter and sugar, then add eggs, milk, flour, baking powder, and vanilla extract until combined.
Pour the prepared batter over the pineapple and cherries in each muffin tin, filling each cup about two-thirds full.

Now it’s time to bake the cupcakes:

Place the muffin tin in the preheated oven and bake for 18-22 minutes or until a toothpick inserted in the center of a cupcake comes out clean.
Let the cupcakes cool in the pan for 5-10 minutes. Carefully run a knife around each cupcake’s edge to loosen it before inverting the pan onto a tray or cooling rack.

For the best presentation and flavor:

Serve the cupcakes while slightly warm to enjoy the gooey caramel glaze.
If desired, add a dollop of whipped cream or a sprinkle of powdered sugar on top for extra indulgence.