Preheat your oven to 350°F (175°C). Spray your muffin tins—either jumbo or regular size—with non-stick cooking spray to prevent the cakes from sticking. This step ensures easy removal and intact presentation later.
In a mixing bowl, combine the eggs, granulated sugar, and pineapple juice. Beat this mixture for 2 minutes until well blended and slightly frothy. In a separate bowl, sift together the flour, baking powder, and salt to ensure even distribution and prevent lumps. Add the dry ingredients to the wet mixture and beat for another 2 minutes until a smooth batter forms. I like to mix just until the ingredients are combined to keep the cakes tender.
In a small saucepan over low heat, melt the butter. Stir in the packed brown sugar and cook for about 1 minute, making sure the mixture is smooth and fully combined. This step creates the signature caramelized topping for the pineapple upside-down cakes.
Spoon a layer of the warm brown sugar mixture from Step 3 into the bottom of each prepared muffin cup. Lay a pineapple ring on top of the brown sugar; if using a standard muffin tin, you may need to trim the pineapple ring to fit, or use tidbits instead. Place a maraschino cherry in the center of each pineapple ring. Finally, pour the cake batter from Step 2 over the fruit layers, filling each muffin cup about 3/4 full. I find that tapping the tin lightly on the counter helps settle the batter evenly around the fruit.
Bake the assembled mini cakes in the preheated oven—25 minutes for jumbo muffins or 20 minutes for regular size. The cakes are done when a toothpick inserted into the center comes out clean. Remove the cakes from the oven and set the pan on a wire rack, allowing them to cool for 3 minutes. Run a knife around the edges of each cake to loosen, then place a wire rack on top of the tin and quickly invert it to release the cakes. Place a sheet tray underneath to catch any drippings. Allow the cakes to cool on the rack before serving. I like to serve these warm, but they're just as delicious at room temperature!