Ingredients
For the topping:
1/2 cup (1 stick) unsalted butter, melted
2/3 cup light brown sugar, packed
12 pineapple rings (canned, drained well and patted dry)
12 maraschino cherries, patted dry
For the cookie dough:
1 cup (2 sticks) unsalted butter, softened to room temperature
1 cup granulated sugar
1 large egg
1 teaspoon vanilla extract
2 1/4 cups all-purpose flour
1/2 teaspoon baking soda
1/2 teaspoon baking powder
1/4 teaspoon salt
Instructions
- Prep the pans
Preheat oven to 350°F (175°C).
Spray a 12-cup muffin tin with nonstick spray (or grease well).
- Make the caramel topping
In a small bowl, mix melted butter and brown sugar.
Place about 1 tablespoon of the mixture into each muffin cup.
Add a pineapple ring on top, trimming to fit if needed.
Place a maraschino cherry in the center hole of each ring.
- Make the cookie dough
In a large mixing bowl, beat the butter and sugar together until light and fluffy (about 2 minutes).
Beat in the egg and vanilla until smooth.
In a separate bowl, whisk together the flour, baking soda, baking powder, and salt.
Gradually mix dry ingredients into the wet until just combined.
- Assemble
Scoop about 2 tablespoons of cookie dough and flatten slightly into a disk.
Place over each pineapple-cherry setup in the muffin cups, spreading gently to cover.
- Bake
Bake for 18–22 minutes, or until the cookies are golden and set.
Let cool for 5 minutes only (important – they’ll stick if too cool).
- Invert & serve
Run a knife gently around edges.
Place a baking sheet or tray on top of the muffin tin and carefully invert to release the cookies.
Serve warm or at room temperature.
Tips:
Pat pineapples and cherries very dry with paper towels so the cookies don’t get soggy.
Best eaten the same day, but can be stored covered at room temp for 1–2 days.
Add a drizzle of caramel sauce or whipped cream for extra indulgence.