1-First Step: Set up the pan and oven Preheat your oven to 350°F (175°C). Choose a 9.5 to 10 inch pie plate, since that size gives the cake enough room to bake evenly and still hold the pineapple pattern nicely. Pour the 60 g melted salted butter into the pan and tilt it so the butter coats the sides as well as the bottom. This helps the cake release more easily later and gives the topping a rich flavor. Next, sprinkle the 100 g packed brown sugar evenly over the butter. Try to cover the whole bottom of the dish so every slice gets a caramel layer. After that, arrange the 10 pineapple slices on top in a single layer. Place the maraschino cherries in the center of the slices or in any empty spots you like.

2-Second Step: Mix the cake batter In a large mixing bowl, beat the 115 g softened unsalted butter and 150 g granulated sugar until the mixture looks creamy and light. This step helps build a soft cake texture. Add the 2 large eggs one at a time, mixing after each addition so the batter stays smooth. Stir in the 1 teaspoon vanilla extract. In a separate bowl, whisk together the 195 g all-purpose flour, 1 1/2 teaspoons baking powder, and 1/4 teaspoon salt. Keeping the dry ingredients separate first helps them mix in more evenly. Then alternate adding the dry mixture and the 120 ml whole milk to the butter mixture, beginning and ending with the dry ingredients. Stir just until combined so the cake stays tender.

3-Third Step: Pour and level the batter Carefully spoon or pour the batter over the fruit layer in the pan. Spread it gently with a spatula so it reaches the edges and covers the pineapple in an even layer. Take your time here, because a smooth surface helps the cake bake evenly and makes the flip look neat. If you are using a cast iron skillet, it can work nicely too, though it may bake a little faster.

4-Fourth Step: Bake with close attention Bake for 30 minutes first. At that point, check the top color. If it is browning too quickly, loosely cover the pan with foil. Then bake for another 15 minutes, or until a toothpick inserted into the center comes out mostly clean. The full baking time is about 45 minutes, but oven temperatures can vary a bit, so the toothpick test matters most.

5-Final Step: Cool, flip, and serve Once the cake is done, let it cool in the pan for 10 to 15 minutes. This short rest helps the topping set just enough so it does not slide apart when you turn it over. Run a knife around the edges to loosen the sides. Then place a serving platter over the pan, hold both firmly, and invert it in one smooth motion. If any pineapple or cherries shift, simply nudge them back into place. Serve warm if you can, since that is when the buttery topping and soft vanilla cake taste best. This is the kind of dessert that feels right after dinner, for weekend guests, or with coffee in the afternoon.