Step 1: Preheat the Oven. Start by preheating your oven to 350°F (175°C). This ensures your cake bakes evenly.
Step 2: Prepare the Topping. In your 9-inch round cake pan, melt the 1/4 cup of butter in the oven. Once melted, sprinkle the 1 cup of brown sugar evenly over the butter, stirring gently to combine.
Step 3: Arrange the Pineapple and Cherries. Place the drained sliced pineapple over the brown sugar mixture, creating a beautiful pattern. Nestle the maraschino cherries in between the pineapple slices for a festive touch.
Step 4: Mix the Cake Batter. In a large mixing bowl, combine the white cake mix, 3 eggs, 1 cup of reserved pineapple juice, 1/2 cup of vegetable oil, and 1 teaspoon of vanilla extract. Using a spatula, mix until smooth and well combined.
Step 5: Pour the Batter. Gently pour the cake batter over the arranged pineapple and cherries in the cake pan. Use a spatula to spread it evenly.
Step 6: Bake the Cake. Place the cake in the preheated oven and bake for 30 to 35 minutes, or until a toothpick inserted into the center comes out clean.
Step 7: Cool and Flip. Allow the cake to cool in the pan for about 10 minutes. Carefully run a knife around the edges, then place a serving plate on top of the cake pan and flip it over to release the cake. Be cautious, as the caramel will be hot!