Ultimate Pineapple Upside-Down Cake

Ingredients

Preheat the oven to 350°F (175°C). Grease a 9-inch (23 cm) round cake pan or cast-iron skillet.
Pour the melted butter into the prepared pan and spread it evenly. Sprinkle the brown sugar over the butter.
Arrange the pineapple rings over the brown sugar and place a maraschino cherry in the center of each ring.
In a medium bowl, whisk together the flour, baking powder, and salt.
In a large bowl, beat the softened butter and granulated sugar until light and fluffy, about 3–4 minutes.
Beat in the eggs one at a time, then add the vanilla extract.
Mix in the reserved pineapple juice.
Add the flour mixture in three additions, alternating with the milk, beginning and ending with the flour. Mix just until combined.
Carefully spread the batter over the pineapple layer without disturbing the fruit.
Bake for 40–45 minutes, or until a toothpick inserted into the center comes out clean.
Cool the cake in the pan for 10 minutes.
Run a knife around the edge, place a serving plate over the pan, and carefully invert the cake onto the plate. Let the pan sit for 1 minute before lifting it off.

Pat the pineapple rings dry to help the caramel topping set properly.
Don’t let the cake cool completely before flipping, or the topping may stick to the pan.
Use room-temperature ingredients for a lighter, fluffier cake.
A cast-iron skillet creates beautifully caramelized edges.

Room Temperature: Store covered for up to 2 days.
Refrigerator: Store for up to 5 days.
Freezer: Freeze individual slices for up to 2 months. Thaw overnight in the refrigerator before serving.

Prep Time: 20 minutes
Cook Time: 40–45 minutes
Cooling Time: 10 minutes
Total Time: About 1 hour 15 minutes
Servings: 8–10 slices