1-First Step: Prepare the pan and oven Preheat your oven to 350°F. Pour the melted salted butter into a 9.5 to 10 inch pie plate, then spread it so the bottom and sides are coated. This buttery layer helps create the caramel topping and helps the cake release after baking. Sprinkle the packed brown sugar evenly over the butter so every bite has sweet, golden flavor.

2-Second Step: Arrange the pineapple and cherries Place the pineapple slices on the bottom and up the sides of the pie plate. Add maraschino cherries in the centers of the pineapple rings and in any empty spaces. If a slice seems too wet, blot it again with paper towels before placing it in the pan. That small step helps prevent a soggy pineapple upside down cake and keeps the topping neat.

3-Third Step: Mix the cake batter In a large bowl, beat the softened unsalted butter and granulated sugar until the mixture looks creamy and pale. Add the eggs one at a time, mixing after each addition, then stir in the vanilla extract. In a separate bowl, whisk together the flour, baking powder, and salt. This helps distribute the leavening evenly so the cake bakes up nicely.

4-Fourth Step: Combine the wet and dry ingredients Add the dry mixture and whole milk to the butter mixture in alternating additions. Start with a portion of the flour mixture, then a splash of milk, and repeat until everything is just combined. Mix only until no dry streaks remain. Over-mixing can make the cake dense or dry, and this recipe works best with a light hand.

5-Fifth Step: Add the batter to the fruit layer Spoon the batter over the pineapple and cherry layer in the pie plate. Spread it gently with a spatula so the surface is even. Try not to press too hard, because you want to keep the fruit arrangement in place underneath. This is where the cake starts to take on that classic upside down look that makes it so inviting.

6-Sixth Step: Bake until golden Bake for 30 minutes, then loosely cover the top with foil if it is browning too quickly. Continue baking for about 15 more minutes, or until a toothpick inserted in the center comes out mostly clean. The total cook time is 45 minutes, and the full recipe time is about 1 hour 10 minutes, including the 25 minute prep time. If you want another cozy baking idea for your dessert lineup, try this caramel pecan sticky buns recipe for a similar buttery, sweet flavor profile.

7-Final Step: Cool and flip Let the cake cool for 10 to 15 minutes before turning it out. Run a knife around the edges to loosen the cake, then place a platter over the top of the pie plate and invert it in one quick motion. Lift the pan away carefully. If a piece of pineapple stays behind, place it back into the warm topping. Serve the cake warm or at room temperature for the best flavor and texture.