Prep the pan and oven: Heat oven to 350°F (175°C). Lightly grease a 12-cup muffin tin with nonstick spray or butter. Cut 6 pineapple rings in half to fit the cups better. Pat them dry with paper towels to reduce excess moisture.

Make the caramel base: Melt 1/2 cup unsalted butter in a small saucepan over low heat. Stir in 2/3 cup packed light brown sugar until glossy and combined. Spoon about 1 tablespoon of this mixture into the bottom of each muffin cup.

Add fruit: Place a maraschino cherry in the center of each cup. Arrange a pineapple half-moon around the cherry. If your cups are roomy, tuck a small extra piece of pineapple to fill gaps, but don’t overpack.

Mix dry ingredients: In a medium bowl, whisk 1 1/2 cups all-purpose flour, 1 1/2 teaspoons baking powder, and 1/2 teaspoon kosher salt.

Cream butter and sugar: In a large bowl, beat 1/2 cup softened unsalted butter with 2/3 cup granulated sugar until light and fluffy, about 2 minutes. This helps create lift and a soft crumb.

Add eggs and vanilla: Beat in 2 large eggs, one at a time, then 2 teaspoons vanilla extract. Scrape the bowl so everything mixes evenly.

Stir in wet ingredients: Add 1/3 cup sour cream and 1/4 cup pineapple juice. If you like an extra-moist cupcake, add 1 tablespoon neutral oil. Mix just to combine.

Combine batter: Add the dry ingredients to the wet in two additions, mixing gently until no dry streaks remain. Do not overmix; a few small lumps are fine.

Fill the cups: Divide the batter evenly among the 12 cups, filling each about 3/4 full. The batter will sit over the fruit and caramel layer.

Bake: Place the pan on the center rack and bake 18–22 minutes. The tops should be golden and spring back when touched. A toothpick should come out mostly clean, with a few moist crumbs.

Cool briefly and invert: Let the cupcakes rest in the pan for 5 minutes to settle. Run a thin knife around the edges. Place a baking sheet or large tray over the muffin pan and carefully invert. Tap the bottom to release. Lift off the pan to reveal glossy, caramel-topped cupcakes.

Serve warm or cool: These taste fantastic slightly warm, when the caramel is still soft. If serving later, let them cool completely on a rack so the topping sets.