1-First Step: Get the pan and oven ready Start by preheating your oven to 350°F. This gives the cake a steady baking temperature from the moment it goes in. Use a 9.5 to 10 inch pie plate, and pour in the 1/4 cup melted salted butter, making sure it coats the bottom and sides of the pan. This helps the topping release later and keeps the fruit layer glossy and rich. Sprinkle the 1/2 cup packed brown sugar evenly over the butter. The sugar will melt as the cake bakes and create that beautiful caramel layer. If you are using a cast iron skillet, this step works well there too, but check the cake a little earlier because cast iron heats faster.

2-Second Step: Build the fruit layer Arrange the 10 pineapple slices over the brown sugar layer. Pat them dry first with paper towels so extra juice does not soak into the cake. Add maraschino cherries in the center of the pineapple rings and in any open spots you want to fill. This gives the finished cake its classic look.

3-Third Step: Make the cake batter In a large mixing bowl, beat the 1/2 cup softened unsalted butter with the 3/4 cup granulated sugar until the mixture looks creamy and pale. Add the 2 large eggs one at a time, mixing after each one. Stir in 1 teaspoon vanilla extract. In a second bowl, whisk together the 1 1/2 cups all-purpose flour, 1 1/2 teaspoons baking powder, and 1/4 teaspoon salt. This helps spread the leavening evenly through the batter. If you want a slightly different flavor, you can replace the whole milk with pineapple juice, which adds a mild fruit note.

4-Fourth Step: Combine the wet and dry ingredients Alternate adding the flour mixture and the 1/2 cup whole milk to the butter mixture. Start with a little flour, then some milk, and keep going until everything is combined. Mix gently and stop as soon as the batter looks smooth. Over-mixing can make the cake dense instead of soft. The batter should be thick but spreadable. If it seems too stiff, check that your butter was softened properly and that you measured the flour correctly. A light hand here makes a big difference in the final crumb.

5-Fifth Step: Add the batter and bake Pour the batter over the fruit layer and spread it gently so it reaches the edges of the pan. Bake for 30 minutes, then loosely cover the top with foil. Continue baking for another 15 minutes, or until a toothpick inserted in the center comes out mostly clean. The foil helps keep the top from browning too quickly while the center finishes baking. If you are baking in a cast iron pan, begin checking around 30 to 35 minutes total since it may bake faster than a glass pie plate. The goal is a golden top, a set center, and a caramelized fruit base that is not overdone.

6-Final Step: Cool, flip, and serve Let the cake cool for 10 to 15 minutes before inverting. This step matters because the topping needs a little time to set, but not so long that it sticks. Run a knife around the edges first to loosen any bits that may be clinging to the pan. Place a serving platter over the pie plate, hold both firmly with oven mitts, and flip in one confident motion. Lift the pan away slowly. If any fruit sticks, you can place it back on top. Serve the cake warm for the best flavor and texture. A warm slice of delicious pineapple upside down cake is hard to beat.