Pineapple Upside-Down Cupcakes

April 11, 2026

Prep time: 10 minutes | Bake time: 20–25 minutes | Yields: 12–24 cupcakes

Ingredients

1 box Yellow Cake Mix (or Pineapple Supreme mix)
Ingredients for cake mix: (Usually 3 eggs, 1/2 cup oil, and water—Pro Tip: Replace the water with the reserved pineapple juice from the can!)
1 can (20 oz) Sliced pineapple (drained, juice reserved)
1 jar Maraschino cherries
1/2 cup Unsalted butter, melted
1 cup Light brown sugar, packed

Instructions

Preheat & Prep: Preheat your oven to 350°F (175°C). Generously spray a muffin tin with non-stick cooking spray.
The Caramel Base: In a small bowl, mix the melted butter and brown sugar. Spoon about 1 tablespoon of this mixture into the bottom of each muffin cup.
The Fruit Layer: * If using pineapple slices, you may need to cut them into smaller pieces to fit the bottom of the muffin tin, or use pineapple tidbits.
Place one piece of pineapple on top of the brown sugar mixture in each cup.
Place one maraschino cherry in the center of the pineapple.
The Cake Batter: Prepare the cake mix according to the box instructions. For extra flavor, use the reserved pineapple juice in place of the water called for on the box.
Fill: Pour the batter into each muffin cup until it is about 2/3 full, covering the pineapple and cherry.
Bake: Bake for 20–25 minutes or until a toothpick inserted into the cake part comes out clean.
The Flip (Crucial Step): Let the cupcakes cool in the pan for only 5 minutes. Run a knife around the edges, place a tray or cookie sheet over the muffin tin, and carefully flip them over. If you wait too long, the sugar will harden and the pineapple will stick to the pan!

Why These are a Treasure

Individual Portions: No messy slicing required—perfect for dinner parties or potlucks.
Built-in Sauce: The butter and brown sugar create a natural caramel glaze that soaks into the cake as it bakes.
Tropical Vibes: They look like little jewels on a serving platter.