Classic Pineapple Upside-Down Sugar Cookies

A playful twist on a classic dessert, these soft sugar cookies are topped with pineapple rings that caramelize as they bake, creating a mini pineapple upside-down cake experience in cookie form.

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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 – ½ teaspoon
• Canned pineapple rings, drained and patted dry – 10–12 rings
• Extra granulated sugar – for sprinkling

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👩‍🍳 Instructions

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

Step 2: Cream the Butter and Sugar
In a large bowl, beat the softened butter and sugar together until pale and fluffy, about 2–3 minutes.

Step 3: Add Wet Ingredients
Beat in the egg and vanilla extract until smooth and fully combined.

Step 4: Combine Dry Ingredients
In a separate bowl, whisk together the flour, baking soda, and salt. Gradually mix the dry ingredients into the butter mixture until a soft dough forms.

Step 5: Shape and Top the Cookies
Scoop about 2 tablespoons of dough onto the prepared baking sheets, spacing them about 2 inches apart.
Gently press a pineapple ring onto each portion of dough, flattening slightly. Cut the rings as needed to fit.

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

Step 7: Cool and Enjoy
Allow the cookies to cool on the baking sheet for a few minutes before transferring them to a wire rack to cool completely.