Pineapple Upside Down Cake

Step 1

Set the oven to 350°F and wait until the indicator light or beep tells you it has finished heating, about 10 minutes.

Step 2

Place a 9-inch round cake pan on the stovetop over medium heat and add 4 tablespoons of butter to the pan.

Step 3

Stir the butter constantly as it melts, then add 0.5 cup of brown sugar to the pan and stir until the sugar dissolves and the mixture turns amber-colored, about 2 minutes.

Step 4

Remove the pan from the heat and pour out any juice from the pineapple can into a measuring cup; set the juice aside.

Step 5

Arrange the drained pineapple rings in a single layer across the bottom of the pan, covering as much of the caramel as possible.

Step 6

Place one maraschino cherry in the center hole of each pineapple ring, or tuck cherries into the gaps between rings.

Step 7

In a medium bowl, whisk together 1.5 cups of flour and 1.5 teaspoons of baking powder until no lumps remain.

Step 8

In a large bowl, add 0.5 cup of softened butter and 1 cup of granulated sugar, then beat with an electric mixer on medium speed until the mixture looks pale and fluffy, about 3 minutes.

Step 9

Crack the two eggs into the bowl one at a time, beating on medium speed for 30 seconds after each egg until fully combined.

Step 10

Pour in 1 teaspoon of vanilla extract and beat on medium speed for 15 seconds until the batter looks smooth.

Step 11

Sprinkle the flour mixture over the batter, then stir with a wooden spoon just until no white streaks of flour are visible—do not overmix.

Step 12

Measure out 0.25 cup of pineapple juice and stir it into the batter until the batter looks smooth and pourable, like thick pancake batter.

Step 13

Pour the batter slowly and evenly over the pineapple and caramel in the pan, using a rubber spatula to gently spread it to the edges so the pineapple stays in place.

Step 14

Set the pan on the middle oven rack and bake until a wooden toothpick inserted into the center of the cake comes out clean or with just a few moist crumbs, about 35 minutes.

Step 15

Remove the pan from the oven using oven mitts and let it sit at room temperature for 5 minutes so the caramel softens slightly.

Step 16

Run a thin knife around the inside edge of the pan to loosen the cake from the sides.

Step 17

Place a serving plate upside down on top of the pan, then hold the plate and pan firmly and flip them together—the cake should slide onto the plate with the pineapple on top.

Step 18

If any caramel is still stuck in the pan, use a rubber spatula to scrape it out onto the top of the cake and smooth it over the pineapple.

Step 19

Let the cake cool to room temperature, about 30 minutes, before slicing and serving.