01 -
Set your oven to 350°F (175°C) and preheat it. Coat the inside of a 12-cup muffin tin with some grease to keep things from sticking.
02 -
Stir the melted butter with the brown sugar in a small bowl until they're totally blended. Split the mix evenly into the muffin tin cups to form a caramel base.
03 -
Put one pineapple ring into each muffin cup, laying it over the caramel mix. Drop a maraschino cherry into the center of each pineapple slice.
04 -
Whip the softened butter and white sugar together until fluffy and smooth. Beat in the eggs one by one, then mix in the vanilla. In a different bowl, combine the flour, baking powder, and salt. Slowly add the dry mix and the milk to the butter-sugar mixture, alternating between them, beginning and ending with the dry stuff. Gently mix in the vegetable oil at the end.
05 -
Scoop the batter on top of the pineapple and cherries, filling each cup until it’s about 3/4 full. Bake the cupcakes for 20–25 minutes until a toothpick stuck in the center comes out clean.
06 -
Let the cupcakes cool in the pan for a bit, about 5 minutes. Then, carefully flip them out onto a rack while they’re still warm so the topping doesn’t stick. Cool them all the way before eating.