Preheat oven to 350°F (175°C). In a medium skillet, melt 6 tablespoons of unsalted butter and add ¼ cup of brown sugar, stirring until smooth and bubbly. Pour this mixture into the bottom of a 9-inch round cake pan, ensuring an even layer. Arrange 10 canned pineapple rings on top, placing a maraschino cherry in the center of each ring.

In a large mixing bowl, whisk together 1 ¾ cups cake flour, 1 teaspoon baking powder, and ¼ teaspoon salt until well combined. Set aside.

In another bowl, cream 6 tablespoons of softened unsalted butter and ¾ cup granulated sugar together using an electric mixer until pale and fluffy. Add 2 eggs one at a time, ensuring each is fully incorporated.

Slowly mix the dry ingredients into the creamed butter and sugar mixture, alternating with ⅓ cup of milk, mixing until just combined.

Pour the batter over the pineapple topping in the cake pan, spreading it evenly. Bake for 45 minutes until edges pull away and a toothpick inserted comes out clean.

Let the cake cool in the pan for about 10 minutes. Run a knife around the edges, then flip onto a serving plate.