1-First step: Prep the pan and oven Start by preheating your oven to 350°F. This is important because the batter should go into a fully heated oven so it starts baking right away. Use a 9.5 to 10 inch pie plate, which gives the fruit and cake enough room to bake evenly. If you are using a different pan, make sure it is deep enough to hold the fruit layer without spilling. Pour the 1/4 cup melted salted butter into the pie plate and spread it up the sides. Then sprinkle the 1/2 cup packed brown sugar evenly over the butter. This becomes the sweet base that turns into the glossy topping when the cake is flipped later. If you like a richer topping, do not leave any dry spots in the sugar layer.

2-Second step: Arrange the fruit Place the 10 pineapple slices over the brown sugar layer. Try to arrange them so the pan is covered in a neat pattern. Put one maraschino cherry in the center of each pineapple ring, or in the open spaces if you are using pineapple slices with smaller centers. The goal is a pretty top that will become the finished face of the cake after inverting. Be sure to blot the pineapple slices with paper towels first. This small step helps reduce sogginess and gives the final cake a better texture. If you use fruit that is too wet, the topping can become watery and the cake may not set as nicely.

3-Third step: Mix the butter and sugar In a large mixing bowl, beat the 1/2 cup softened unsalted butter and 3/4 cup granulated sugar until the mixture looks creamy and fluffy. This helps give the cake a lighter texture. Once that is mixed, add the 2 large eggs one at a time, mixing after each addition. This slow addition helps the batter stay smooth. Next, stir in 1 teaspoon vanilla extract. The vanilla gives the cake its classic warm flavor and works beautifully with the pineapple topping. Keep the mixing gentle once the eggs are in place, because too much beating can make the crumb dense.

4-Fourth step: Combine the dry ingredients In another bowl, whisk together 1 1/2 cups all-purpose flour, 1 1/2 teaspoons baking powder, and 1/4 teaspoon salt. This keeps the leavening evenly distributed so the cake rises properly. A quick whisk also helps break up any lumps in the flour. If you need a gluten-free version, this is the point where you would swap in a 1:1 gluten-free flour blend. The rest of the process stays the same, though bake time may vary a little depending on the blend you choose.

5-Fifth step: Finish the batter Now add the dry ingredients to the wet mixture in alternating additions with 1/2 cup whole milk at room temperature. Start with a little flour mixture, then add a little milk, and keep going until everything is combined. This method helps the batter stay smooth and prevents overmixing. The batter should look thick but easy to pour. If you want to use pineapple juice instead of milk, you can, but milk is recommended for the best texture. Avoid whipping the batter for too long, since that can make the cake heavy instead of soft.

6-Sixth step: Layer and bake Carefully pour the batter over the fruit layer in the pie plate. Spread it gently so the fruit stays in place underneath. Slide the pan into the oven and bake for 30 minutes. At that point, loosely cover the top with foil and bake for another 15 minutes, or until a toothpick inserted in the center comes out clean. Checking the cake after 30 minutes matters because it helps prevent over-browning. Every oven runs a little differently, so keep an eye on the color as it bakes. If the top looks very dark before the center is done, the foil will help protect it.

7-Seventh step: Cool and invert When the cake is done, let it cool for 10 to 15 minutes. This cooling time is important because the topping needs a moment to settle before you flip the cake. If you turn it out too soon, the fruit may slide around. If you wait too long, the caramel topping can stick to the pan. Place a serving platter over the pie plate, wear oven mitts, and invert the cake in one steady motion. If needed, loosen the edges with a knife before flipping. Lift the pan slowly and let the beautiful pineapple topping reveal itself. The cake tastes best warm and fresh, especially with a simple cup of coffee or tea.

8-Final step: Serve and enjoy After you remove the pan, check if any pineapple or cherry pieces need to be set back into place. A small gentle touch is usually enough. Slice the cake while it is still warm for the softest texture. If you are serving guests, add a spoonful of whipped cream or a scoop of vanilla ice cream on the side.