Pineapple Upside-Down Cake

Total Time: 1 hour 15 minutes
- Prep Time: 25 minutes
- Cook Time: 45-50 minutes
Yield: One 9-inch cake (8-10 servings)
Skill Level: Beginner to Intermediate
Intensity: Medium (requires careful attention during the caramelizing and flipping steps)

Preheat your oven to 350°F (175°C). Do not grease the cake pan. The topping creates its own non-stick layer.

In a medium saucepan over medium heat, melt ½ cup of butter.
Stir in the brown sugar and cook, stirring constantly, for about 2-3 minutes until the mixture is bubbly and the sugar has mostly dissolved. It will look like a thick, grainy sauce. Do not boil for longer than this.
Immediately pour the hot butter-sugar mixture into the bottom of your ungreased cake pan. Using a heat-proof spatula, spread it into a relatively even layer.
Drain the pineapple rings, reserving 2 tablespoons of the juice for the batter. Blot the rings lightly with a paper towel to remove excess juice.
Arrange the pineapple rings in a single layer on top of the caramel. You can fit about 7 rings around the edge and one in the center if space allows. Place a maraschino cherry in the center of each ring and in any gaps between rings. Set the pan aside.

In a medium bowl, whisk together the flour, baking powder, baking soda, and salt. Set aside.
In a large bowl using an electric mixer, beat the softened ½ cup of butter and granulated sugar together on medium-high speed for 2-3 minutes, until light and fluffy.
Add the eggs one at a time, beating well after each addition. Scrape down the sides of the bowl. Beat in the vanilla extract.
With the mixer on low, add the dry ingredients in three parts, alternating with the milk and the 2 tablespoons of reserved pineapple juice, beginning and ending with the dry ingredients. Mix only until just combined. Do not overmix.

Carefully spoon the thick cake batter over the arranged pineapple and cherries in the pan. Use a spatula to gently spread it into an even layer, being careful not to disturb the fruit pattern underneath.
Place the pan on the center rack of the preheated oven. Bake for 45-50 minutes, or until a toothpick inserted into the center of the cake (through the batter) comes out clean. The top will be golden brown, and the caramel will be bubbling around the edges.

Remove the cake from the oven and place it on a wire cooling rack. Let it cool in the pan for only 10 minutes. This is the most important step. Cooling too long will cause the caramel to harden and stick to the pan.
After 10 minutes, run a thin knife or offset spatula around the edges of the cake to loosen it from the sides.
Place a large, heat-proof serving plate or platter upside-down over the top of the cake pan. Using oven mitts (the pan is still hot!), firmly hold the plate and pan together and flip them over in one confident, swift motion.
Gently lift the cake pan away. If any fruit sticks, carefully remove it with a spatula and place it back on the cake.
Allow the cake to cool for at least 30 minutes before slicing. The caramel topping will set as it cools.

Room Temperature is Key: Using room-temperature eggs, milk, and butter ensures a smooth, well-emulsified batter that bakes evenly.
Don’t Overmix: Overmixing the batter develops gluten, leading to a tough, dense cake. Mix just until the flour disappears.
The 10-Minute Rule: Do not skip or extend the 10-minute cooling period before flipping. This allows the caramel to set just enough to hold its shape but not so much that it bonds to the pan.
Serve It Right: This cake is best served slightly warm or at room temperature on the day it is made. A dollop of freshly whipped cream or a scoop of vanilla ice cream is a perfect pairing.