Description

These pineapple upside-down sugar cookies combine all the tropical goodness of the classic dessert with soft, chewy sugar cookies. Topped with caramelized pineapple and a cherry, each cookie is a little bite of sunshine. They’re perfect for parties, potlucks, or just when you’re craving something fruity and fun!

Ingredients

Topping:

1/4 cup unsalted butter, melted
1/2 cup light brown sugar
10 maraschino cherries, halved
1 cup canned pineapple tidbits or chopped rings, drained and patted dry

Cookies:

1 cup unsalted butter, softened
1 cup granulated sugar
1 large egg
2 teaspoons vanilla extract
2 1/2 cups all-purpose flour
1/2 teaspoon baking soda
1/4 teaspoon salt

Cook Mode Prevent your screen from going dark

Instructions

Preheat oven: Preheat to 350°F (175°C). Lightly grease a muffin tin (standard size).
Make topping: In a small bowl, mix melted butter and brown sugar. Spoon about 1 teaspoon into the bottom of each muffin cup. Add a few pineapple pieces and half a maraschino cherry on top.
Make cookie dough: In a large bowl, cream together softened butter and sugar until light and fluffy. Beat in the egg and vanilla. In a separate bowl, whisk flour, baking soda, and salt. Gradually add dry ingredients to the wet, mixing until combined.
Assemble: Scoop about 1 ½ tablespoons of cookie dough and gently press it on top of the fruit in each muffin cup, flattening slightly.
Bake: Bake for 12–14 minutes, or until edges are just golden.
Cool and flip: Let cookies cool in the pan for 5 minutes. Carefully run a knife around the edges and invert the muffin tin onto a wire rack to release the cookies.
Serve: Let cool completely or enjoy slightly warm.

Notes

Be sure the pineapple is well-drained to avoid soggy cookies.
These cookies are best enjoyed the day they’re made but can be stored in an airtight container for up to 3 days.
You can use mini muffin tins for bite-sized versions — just reduce the bake time by a few minutes.