Why You’ll Love This Recipe

• Easy to make with a box of yellow cake mix.
• Beautiful presentation thanks to caramelized fruit topping.
• Moist, flavorful, and fun-sized—perfect for sharing!

Ingredients and Their Purpose

• 1 can (20 oz) sliced pineapple – Provides tropical flavor and a juicy, caramelized topping. Drain and reserve the juice.
• 1 box yellow cake mix – Offers a quick and consistent base that’s rich and buttery.
• 1/2 cup vegetable oil – Adds moisture and helps create a tender crumb.
• 3 large eggs – Bind the ingredients together and add richness.
• 1/3 cup butter, melted – Creates the rich caramel layer when combined with brown sugar.
• 2/3 cup packed brown sugar – Sweetens the bottom layer, which becomes the gooey, golden top when flipped.
• 12 maraschino cherries (halved) – Add a pop of color and classic sweetness.

How to Make Pineapple Upside Down Cupcakes

Step 1: Preheat and Prepare

Preheat your oven to 350°F (175°C). Line a muffin tin with cupcake liners or spray generously with non-stick baking spray.

Step 2: Create the Caramel Fruit Layer

1. Melt the butter in the microwave or on the stove.
2. Divide the brown sugar evenly among the bottom of each cupcake liner—about 1 tablespoon per liner.
3. Spoon melted butter (about 1 teaspoon) over the brown sugar in each liner.
4. Add pineapple slices: Cut each pineapple ring to fit into the muffin wells. Add a piece of pineapple on top of the sugar-butter mixture.
5. Place a cherry half in the center of the pineapple slice, cut-side up.

Step 3: Make the Cake Batter

1. In a large mixing bowl, combine yellow cake mix, eggs, vegetable oil, and 1 cup of reserved pineapple juice.
2. Mix until the batter is smooth and lump-free, about 2 minutes using a hand mixer or whisk.

Step 4: Fill and Bake

1. Carefully spoon the cake batter over the fruit layer, filling each cupcake liner about two-thirds full.
2. Bake in the preheated oven for 20–25 minutes or until a toothpick inserted in the center comes out clean.

Step 5: Cool and Invert

1. Let the cupcakes cool in the pan for 5–10 minutes only—do not wait longer or the topping may stick.
2. Run a knife around the edges if needed and invert the cupcakes onto a wire rack or tray lined with parchment paper.
3. Lift the pan gently—each cupcake should reveal a gorgeous, glossy fruit top.

Pro Tips for the Best Results

• Use fresh maraschino cherries from a new jar for best flavor and color.
• Don’t skip the cupcake liners or grease well if going without—they help with easy release.
• Let cupcakes rest briefly after baking before flipping, but not too long or the sugar will harden.
• Use an ice cream scoop to evenly portion the batter into each liner.
• Store leftovers in an airtight container in the fridge for up to 3 days.

Serving Suggestions

These cupcakes are perfect on their own, but you can also:

• Serve warm with a scoop of vanilla ice cream.
• Add a drizzle of salted caramel sauce for an indulgent twist.
• Top with a dollop of whipped cream and a mint leaf for presentation.