Preheat oven to 350°F (175°C). Grease a 9-inch round cake pan or cast-iron skillet.
- Pour melted butter into the pan and sprinkle evenly with brown sugar. Arrange pineapple rings over the sugar and place a cherry in the center of each ring.
- In a medium bowl, whisk together flour, baking powder, and salt.
- In a large bowl, cream softened butter and granulated sugar until light and fluffy. Add eggs one at a time, beating well after each, then mix in vanilla extract.
- Alternate adding the dry ingredients and the milk/pineapple juice mixture into the wet ingredients, beginning and ending with dry. Mix until just combined.
- Pour the batter over the pineapple topping and smooth the top.
- Bake for 40–45 minutes or until a toothpick inserted in the center comes out clean.
- Let the cake cool in the pan for 10–15 minutes. Run a knife around the edges, then carefully invert onto a serving plate.
- Cool slightly before slicing and serving.