1-First Step: Prepare the pan and oven Start by preheating your oven to 350°F. While the oven heats, add 1/4 cup melted butter to a 9×13-inch baking dish and spread it evenly across the bottom. This buttery layer helps the brown sugar melt into the classic glossy topping that makes pineapple upside down cake so appealing. Next, sprinkle 1 cup brown sugar evenly over the butter. Try to cover the whole bottom of the pan so every slice gets a sweet caramel-like base. If you are using a different size baking dish, grease it well so the cake releases more easily later.

2-Second Step: Arrange the fruit Open the 1 can (20 ounces) sliced pineapple and place the slices over the brown sugar layer. Arrange them in a single layer so the topping looks neat after the cake is flipped. Put 18 maraschino cherries in the center of each pineapple slice. This is the part that gives the dessert its classic look, and it is a fun step if you are baking with kids or family. If you want a fruit-forward dessert with a bright finish, this is where the recipe really shines. The pineapple softens while baking, and the sugar underneath bubbles into a rich topping.

3-Third Step: Mix the batter Pour the pineapple juice from the can into a measuring cup, then add enough water to make 1 cup total. In a large mixing bowl, beat that liquid with 3 eggs and 1/2 cup vegetable oil. Mix until everything looks smooth and well combined. Stir in 1 box (15.25 ounces) yellow cake mix until the batter is smooth and no dry streaks remain. Do not overmix. A smooth batter is enough, and stopping once the flour is combined helps keep the cake soft.

4-Fourth Step: Assemble and bake Pour the batter over the fruit in the pan, then spread it evenly from edge to edge. This helps the cake bake at the same rate and keeps the topping in place. Place the pan in the preheated oven and bake for 45 minutes, or until the top is golden brown and a toothpick inserted into the cake portion comes out mostly clean. Some ovens run hot, so begin checking a few minutes early if you know yours bakes quickly. If you are using a glass dish, the cake may need a small timing adjustment depending on your oven.

5-Final Step: Flip, cool, and serve Once baked, let the cake sit for a few minutes. Then run a knife around the edges to loosen it from the pan. Place a tray or serving platter over the baking dish, hold both firmly, and flip the cake onto the tray in one careful motion. If any fruit shifts, gently place it back where it belongs. Cool for 15 minutes before serving. This short rest helps the topping set a bit so each slice holds together better. The cake is wonderful served warm, but it also tastes great at room temperature. For the best look, flip the cake while it is still warm enough to release easily, but not so hot that the fruit topping slides around.