Preheat your oven to 350°F (175°C). Grease a muffin tin or individual cake pans (for about 6 mini cakes) with butter or cooking spray.
In a small bowl, mix the melted butter and brown sugar until combined. Spoon about 1 tablespoon of this mixture into the bottom of each muffin cup or cake pan.
Place a pineapple ring in each cup (cut the rings if they’re too large to fit). Place a maraschino cherry half in the center of each pineapple ring, or scatter additional cherry halves around the edges for decoration.
2. Make the Cake Batter:
In a medium bowl, whisk together the flour, baking powder, salt, and cinnamon (if using).
In a separate bowl, beat together the softened butter and granulated sugar until light and fluffy, about 2-3 minutes.
Add the egg and vanilla extract, and beat until combined.
Gradually add the dry ingredients to the wet mixture, alternating with the milk (or pineapple juice), mixing until just combined. The batter will be thick.
3. Assemble and Bake:
Spoon the cake batter evenly over the pineapple topping in each muffin cup, filling about 2/3 of the way full.
Bake for 20-25 minutes, or until the tops are golden brown and a toothpick inserted into the center comes out clean.
Remove from the oven and allow to cool in the pan for about 5 minutes.
4. Flip the Cakes:
Once the cakes have cooled slightly, carefully run a knife around the edges of each cake to loosen them.
Place a serving plate over the muffin tin or cake pan, and carefully flip it over to release the cakes. The pineapple topping should be perfectly caramelized and golden.
5. Serve:
Serve warm or at room temperature. You can add a dollop of whipped cream or a scoop of vanilla ice cream on top for extra indulgence.
