Classic Pineapple Upside-Down Sugar Cookies

A fun spin on the traditional cake, these tender sugar cookies are finished with a pineapple ring that caramelizes as they bake, creating a mini pineapple upside-down cake effect in cookie form.

Pineapple Upside-Down Sugar Cookies

Ingredients

• Unsalted butter, softened – 1 cup
• Granulated sugar – 1 cup
• Large egg – 1
• Vanilla extract – 1 teaspoon
• All-purpose flour – 2 cups
• Baking soda – 1 teaspoon
• Salt – 1/2 teaspoon
• Canned pineapple rings, drained and patted dry – 10–12 rings
• Extra granulated sugar – for sprinkling

Instructions

Step 1: Prepare the Oven and Pans
Preheat the oven to 350°F (180°C). Line baking sheets with parchment paper and set aside.

Step 2: Cream Butter and Sugar
In a large mixing bowl, beat the softened butter and sugar together until light and fluffy, about 2–3 minutes using an electric mixer.

Step 3: Add Wet Ingredients
Mix in the egg and vanilla extract, beating until smooth and fully incorporated.

Step 4: Mix Dry Ingredients
In a separate bowl, whisk together the flour, baking soda, and salt. Gradually add this mixture to the wet ingredients, mixing just until a soft dough forms.

Step 5: Shape Cookies and Add Pineapple
Scoop about 2 tablespoons of dough onto the prepared baking sheets, leaving about 2 inches between each. Gently press a dried pineapple ring onto each cookie, flattening slightly. Cut the rings if needed to fit.

Step 6: Sprinkle and Bake
Lightly sprinkle sugar over the pineapple tops. Bake for 11–13 minutes, or until the edges are lightly golden and the centers are set.

Step 7: Cool and Serve
Let the cookies cool on the baking sheet for a few minutes, then transfer to a wire rack to cool completely. Enjoy!