Pineapple Upside-Down Cake

Note: I recommend making this cake in a 9" round cake pan, preferably non-stick, but it can also be made in a 9" skillet.

Preheat oven to 350℉.
Drain pineapple slices, reserving juice in a small bowl. Dry pineapple slices on a large plate lined with paper towel. Set aside.
1 can (at least 13.5oz or 398mL) pineapple slices, in 100% pineapple juice (not syrup)
If baking in a 9" round cake pan, butter bottom and sides of pan. Set aside.
In a frying pan (or in 9" skillet) set over medium heat, combine butter, brown sugar, and dark rum (or pineapple juice, or water). Heat until mixture becomes thick, foamy, and bubbly.
¼ cup (½ stick) unsalted butter
⅓ cup brown sugar, packed
2 Tbsp good-quality dark rum, or reserved pineapple juice, or water
If baking in a cake pan: Pour the caramel from the frying pan into the prepared cake pan, then place it on a wire rack.
If baking in a skillet: Remove the skillet from heat and place it on a wire rack.
Arrange the pineapple slices in the caramel as desired. Fill any gaps with maraschino cherries (stems removed), using as many or as few as desired. Set aside to cool while preparing the cake batter.

In a medium-sized bowl, whisk together flour, baking powder, baking soda, and salt. Set aside.
1 ½ cups all-purpose flour
1 tsp baking powder
¼ tsp baking soda
½ tsp kosher salt
In a glass measuring cup (or small bowl), whisk together sour cream and reserved pineapple juice (or milk, if using fresh pineapple). Set aside.
½ cup full-fat sour cream, at room temperature
¼ cup reserved pineapple juice
In a large bowl, combine butter and sugar. Using an electric hand mixer (or a stand mixer), cream together butter and sugar until the mixture is light yellow and fluffy (about 3 minutes).
½ cup (1 stick) unsalted butter, at room temperature
¾ cup granulated sugar
Add in eggs, one at a time, followed by the vanilla. Mix until well combined, scraping down the sides of the bowl as necessary (about 1 to 2 minutes).
2 large eggs, at room temperature
1 ½ tsp pure vanilla extract
With the mixer on low, alternate adding in the dry and wet ingredients, as follows: ⅓ of the dry mixture (until just combined), ½ of the wet mixture, another ⅓ of the dry mixture (again, until just combined), the remaining ½ of the wet mixture, and finish with the final ⅓ of the dry mixture. (Note: Be careful not to overmix!)
Carefully spoon the cake batter over the arranged fruit. Using an offset spatula (or the back of a spoon), gently spread the batter to evenly cover the surface and create a smooth, level layer.

Set the cake pan on a baking sheet and into the center of preheated oven. Bake until the top of the cake turns golden brown and a toothpick inserted into the center comes out clean (about 40 to 45 minutes).
Remove the cake from the oven and set it on a wire rack. Allow it to cool for 15 minutes — just long enough to cool slightly without allowing the caramel to harden and stick to the pan!
Run a knife around the edge of the pan to loosen the cake. Carefully invert it onto a large serving plate. Allow the cake to cool for at least another 30 minutes before serving.
To store, allow cake to cool completely, cover with plastic wrap, and refrigerate.