Pineapple Upside Down Cupcakes 🍍✨

👩‍🍳 Instructions

Preheat your oven to $350^{\circ}\text{F}$ ( $175^{\circ}\text{C}$ ).
Lightly grease a standard 12-cup muffin tin. Do NOT use cupcake liners, as the caramelized topping needs to stick to the pan.
In a small bowl, combine the melted butter and brown sugar until a paste forms.
Evenly divide the butter-sugar mixture among the 12 muffin cups. You should put about 1 teaspoon into the bottom of each cup.
Place one pineapple slice (or half-slice) on top of the brown sugar mixture in each cup.
Place one well-drained and dried maraschino cherry in the center of the pineapple ring. Set the pan aside.

In a medium bowl, whisk together the flour, baking powder, and salt. Set aside.
In a large bowl, using an electric mixer (handheld or stand mixer with paddle attachment), cream together the softened butter and granulated sugar on medium speed until light and fluffy (about 3-4 minutes).
Beat in the eggs one at a time, mixing well after each addition. Scrape down the sides of the bowl as needed. Add the vanilla extract and mix until combined.
Alternately add the dry ingredients (flour mixture) and the milk to the wet ingredients, beginning and ending with the dry ingredients. Mix on low speed just until combined. Do not overmix! The batter will be thick.

Carefully spoon the cupcake batter over the pineapple and cherry in each cup, filling each cup about $2/3$ full. Be gentle so you don't disturb the topping layer underneath.
Bake for 18-20 minutes, or until a toothpick inserted into the center of a cupcake comes out clean.
Remove the pan from the oven and let the cupcakes cool in the pan for exactly 5 minutes. This is crucial for the topping to set but not harden.

Place a large wire cooling rack (or a flat cutting board) directly over the muffin tin.
Working quickly, flip the entire pan over to invert the cupcakes onto the cooling rack.
If any topping or pineapple slices stick to the pan, use a small offset spatula to gently scoop them out and place them back on top of the corresponding cupcake.
Allow the cupcakes to cool completely on the wire rack before serving.