1
Preheat oven to 350°F. Melt 1/4 cup unsalted butter in a 9-inch cake pan, then swirl to coat the bottom and sides evenly.
2
Sprinkle 1/2 cup light brown sugar evenly over the butter, then tap the pan to distribute it uniformly.
3
Drain the canned pineapple slices and pat them dry with paper towels. Arrange one slice in the center and position the remaining slices around the pan, placing a cherry in the middle of each gap.
4
In a medium bowl, whisk together 1 1/2 cups all-purpose flour, 1 1/2 teaspoons baking powder, and 1/2 teaspoon salt until combined. Set aside.
5
Combine 1/3 cup sour cream and 1/3 cup milk (or reserved pineapple juice) in a separate container and mix until smooth. Set aside.
6
Using a stand mixer or hand mixer, beat 1/2 cup room-temperature unsalted butter until creamy, about 1 minute.
7
Add 3/4 cup granulated sugar and beat on medium speed for about 3 minutes until light and fluffy, scraping down the bowl halfway through.
8
Add the 2 large room-temperature eggs one at a time, scraping the bowl between each addition to ensure they are fully incorporated.
9
Add 2 teaspoons vanilla extract and mix until combined.
10
Add the dry ingredients and sour cream mixture in alternating batches: 1/3 of the dry mixture, 1/2 of the sour cream mixture, 1/3 of the dry mixture, the remaining sour cream mixture, and finally the remaining dry mixture. Mix on low speed until just combined between batches, being careful not to overmix. Finish with a spatula, scraping to ensure no dry streaks remain.
11
Carefully pour the batter into the prepared pan, smoothing it with an offset spatula while being careful not to disturb the pineapple and cherry arrangement. Place the cake pan on a rimmed baking sheet.
12
Bake in the oven at 350°F for 40 to 45 minutes, until a toothpick or skewer inserted in the center comes out clean. If the cake is browning too quickly, cover with foil after about 30 minutes.
13
Let the baked cake cool in the pan for 15 minutes. If needed, run a small knife around the edge, then invert the cake onto a serving plate.
14
After inverting, let the cake cool for about 20 minutes before slicing. This cake is best served warm and pairs beautifully with ice cream.
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