Ingredients 1x2x3x

• 1 box yellow cake mix (15.25 ounces; white or pineapple cake mix also works)
• 3 large eggs (or as directed on the cake mix box)
• 1/2 cup vegetable oil (or as directed on the box)
• 1 cup liquid total for the cake batter: use the juice from the pineapple can plus water to reach 1 cup
• 1/2 cup unsalted butter (1 stick)
• 3/4 to 1 cup packed light brown sugar
• 1 can pineapple rings (20 ounces, in juice, not syrup)
• Maraschino cherries (about 12–16)
• Optional flavors: 1 teaspoon vanilla extract, 1/2 teaspoon almond extract, or a pinch of cinnamon
• Nonstick spray or extra butter for the pan

Method

1. Prep the pan and oven: Heat oven to 350°F (175°C). Grease a 9x13 pan or a deep 12-inch oven-safe skillet. You can also use two 9-inch cake pans.
2. Make the caramel base: Melt the butter in a small saucepan. Stir in the brown sugar until it looks like wet sand and glossy. Pour this mixture evenly into your prepared pan.
3. Arrange the fruit: Lay pineapple rings over the brown sugar mixture. Nestle a cherry into the center of each ring. Fill gaps with halved rings or tidbits so the top looks full and even.
4. Mix the batter: In a bowl, combine cake mix, eggs, oil, and 1 cup total liquid using the pineapple juice plus water. Beat just until smooth—about 30–45 seconds with a hand mixer on medium. Add vanilla or almond extract if using.
5. Pour carefully: Spoon or pour the batter over the fruit. Spread gently to the edges without disturbing the arrangement.
6. Bake: Place on the center rack. Bake 35–45 minutes for a 9x13 pan, 30–38 minutes for 9-inch rounds, or until a toothpick in the center comes out clean and the top is golden.
7. Rest and flip: Cool on a rack for 10–15 minutes. Run a knife around the edges. Invert a serving platter over the pan, then flip in one confident motion. Lift the pan straight up. If any fruit sticks, gently place it back on the cake.
8. Cool and serve: Let the cake sit 15–20 more minutes so the topping sets. Serve warm or at room temperature. A dollop of whipped cream is perfect.

Notes

• Room temperature: Cover loosely and keep up to 2 days. The topping stays soft and glossy.
• Refrigerator: Store covered for up to 5 days. Bring slices to room temperature or warm slightly to revive the texture.
• Freezer: Wrap individual slices tightly and freeze up to 2 months. Thaw in the fridge overnight, then warm briefly.