1. Prepare the Pan and Oven:

Preheat the oven to 350°F (175°C).

Spray a 9×13-inch baking pan with baking spray with flour.

Line the bottom of the pan with parchment paper. Do not spray the parchment paper again.

2. Prepare the Pineapple: Drain the pineapple slices (both cans) and reserve the juice for later use.

Pat the pineapple slices dry with paper towels. This is important to prevent the cake from becoming soggy.

Place the pineapple slices in a large bowl.

Sprinkle the pineapple slices with 2 tablespoons of granulated sugar and the cornstarch. Toss gently to coat.

Arrange the pineapple slices in the prepared pan, fitting them snugly together.

Add the maraschino cherries to the centers of the pineapple rings.

3. Make the Caramel:

In a medium stainless-steel skillet, melt ¾ cup of the softened butter over medium heat.

Stir in the light brown sugar and ½ teaspoon of the kosher salt.

Bring the mixture to a simmer. Cook until the sugar is melted and fragrant, about 3 minutes.

Slowly pour in 3 tablespoons of the reserved pineapple juice, whisking until combined and smooth.

Pour the caramel evenly over the pineapple slices in the pan.

4. Make the Cake Batter: In the bowl of a stand mixer (or using a hand mixer and a large bowl), beat the remaining 1 cup of softened butter, the remaining 2 cups of granulated sugar, the orange zest (if using), and the vanilla extract at medium speed until creamy, 2 to 3 minutes. Stopping occasionally to scrape the sides of the bowl.

Add the eggs, one at a time, beating well after each addition.

In a medium bowl, whisk together the all-purpose flour, baking powder, baking soda, and the remaining 1 teaspoon of kosher salt.

Gradually add the flour mixture to the butter mixture alternately with the sour cream. Beginning and ending with the flour mixture. Beat just until combined after each addition. Be careful not to overmix.

5. Pour Batter over Pineapple and Caramel: Carefully dollop the batter onto the pineapple and caramel in the pan.

Gently spread the batter with an offset spatula or the back of a spoon, making sure not to press too hard or move the pineapple slices.

6. Bake:

Bake for 30 minutes.

Place a piece of foil on top of the cake to prevent excess browning.

Continue baking until a wooden pick inserted into the center of the cake comes out clean, 15 to 20 minutes more.

7. Cool and Invert:

Remove the foil.

Let the cake cool in the pan on a wire rack for 10 minutes.

Run a thin knife or offset spatula around the sides of the cake to loosen it from the pan.

Carefully invert the cake onto a serving plate.

Remove the parchment paper.

Let the cake cool completely.

8. Serve: Serve warm, at room temperature, or cold.

Serve with ice cream or whipped cream, if desired. Enjoy!