Preheat your oven to 350°F (175°C). Use this time to line a muffin tin with paper liners or grease it lightly with oil.
Cream together 1/2 cup softened butter and 1/2 cup brown sugar in a mixing bowl until the mixture is fluffy and light in color, which should take about 2-3 minutes.
Spoon this mixture into the bottom of each muffin cup, distributing it evenly. Place one pineapple ring and one maraschino cherry in the center of each ring on top of the brown sugar/butter mixture.
In another bowl, combine 1 cup all-purpose flour, 1 tsp baking powder, and 1/2 tsp salt. Mix thoroughly and set aside.
In a separate large bowl, beat together 1/2 cup granulated sugar, 1/2 cup milk, 1 large egg, and 1 tsp vanilla extract until smooth.
Gradually add the dry ingredients to the wet mixture, stirring carefully until just combined. Avoid overmixing to keep the cupcakes light and airy.
Spoon the batter over the pineapple rings in the muffin tin, filling each cup about 2/3 full.
Bake in the preheated oven for 20-25 minutes. You’ll know they are done when a toothpick inserted into the center comes out clean.
Once baked, let the cupcakes cool in the pan for about 5 minutes before carefully inverting them onto a wire rack to cool completely. This allows the caramelized topping to set beautifully.