Pineapple Upside Down Sugar Cookies Recipe

Introduction

These Pineapple Upside Down Sugar Cookies offer a delightful twist on a classic dessert. Soft sugar cookies baked atop caramelized pineapple and optional maraschino cherries create a sweet, tangy treat that’s as beautiful as it is delicious. Perfect for any occasion, these cookies bring a tropical vibe to your baking repertoire.

Ingredients

• 2 ½ cups all-purpose flour
• 1 teaspoon baking powder
• ½ teaspoon baking soda
• ½ teaspoon salt
• 1 cup (2 sticks) unsalted butter, softened
• ¾ cup granulated sugar
• ¾ cup packed light brown sugar
• 2 large eggs
• 1 teaspoon vanilla extract
• ½ cup (1 stick) unsalted butter (for topping)
• ¾ cup packed light brown sugar (for topping)
• 1 (20 ounce) can pineapple slices, drained and patted dry
• Maraschino cherries, halved (optional)

Instructions

1. Step 1: Prepare the pineapple topping by melting ½ cup unsalted butter in a medium saucepan over medium heat. Stir in ¾ cup packed light brown sugar until dissolved and the mixture is smooth and glossy, about 2-3 minutes.
2. Step 2: Line a large baking sheet with parchment paper. Pour the caramel mixture evenly onto the sheet and spread into a thin, even layer.
3. Step 3: Arrange the drained pineapple slices on top of the caramel, spacing them about 2 inches apart. Place halved maraschino cherries in the center of each pineapple slice, if using.
4. Step 4: In a medium bowl, whisk together the flour, baking powder, baking soda, and salt to combine evenly.
5. Step 5: In a large bowl, cream the softened butter with granulated sugar and light brown sugar until light and fluffy, about 3-5 minutes.
6. Step 6: Beat in the eggs one at a time, fully incorporating each before adding the next, then stir in the vanilla extract.
7. Step 7: Gradually add the dry ingredients to the wet ingredients, mixing on low speed until just combined. Avoid overmixing.
8. Step 8: Wrap the dough in plastic wrap and chill in the refrigerator for at least 30 minutes to prevent spreading.
9. Step 9: Preheat the oven to 375°F (190°C) and position the oven rack in the center.
10. Step 10: Scoop about 1.5 tablespoons of dough and gently flatten into discs. Place each disc on top of a pineapple slice on the prepared baking sheet, pressing down slightly to adhere.
11. Step 11: Bake for 10-12 minutes, or until the cookie edges are lightly golden brown. Watch carefully to avoid overbaking.
12. Step 12: Let the cookies cool on the baking sheet for 5 minutes to allow the caramel to set slightly, then carefully invert them onto a wire rack to cool completely. Use a thin spatula if needed, but be cautious—the caramel will be hot.

Tips & Variations

• Drain pineapple slices thoroughly to prevent soggy cookies.
• Use softened butter for a lighter, fluffier dough.
• Chill dough well to control spreading during baking.
• Don’t skip parchment paper to ensure easy removal after baking.
• Add a pinch of cinnamon or nutmeg to the cookie dough for warm spice notes.
• Try different fruits like peaches or apricots as a topping variation.
• Sprinkle chopped nuts like pecans or walnuts over the caramel for added texture.
• For a lighter version, substitute part of the butter with applesauce or Greek yogurt.

Storage

Store cooled cookies in an airtight container at room temperature for up to 3 days. To reheat, warm gently in a microwave or oven to bring back the soft texture and caramel warmth.

How to Serve

Serve this delicious recipe with your favorite sides.

FAQs

How do I prevent the cookies from spreading too much?

Chilling the dough for at least 30 minutes is key to control spreading. Also, ensure you measure ingredients accurately and avoid overmixing the dough.

Can I substitute fresh pineapple for canned?

Yes, but make sure to pat fresh pineapple slices very dry to remove excess moisture, which can make the cookies soggy.

Pineapple Upside Down Sugar Cookies Recipe

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★★★★★

4.9 from 149 reviews

Sweet and tangy Pineapple Upside Down Sugar Cookies offer a fun twist on a classic dessert, featuring soft, buttery sugar cookies baked atop a luscious caramelized pineapple and cherry topping. These cookies deliver a delightful contrast of textures and flavors, making them perfect for parties, potlucks, or a special treat.

• Author: Ella
• Prep Time: 30 minutes
• Cook Time: 12 minutes
• Total Time: 60 minutes
• Yield: 16–20 cookies 1x
• Category: Dessert
• Method: Baking
• Cuisine: American
• Diet: Vegetarian

Ingredients

Scale 1x2x3x

For the Cookie Dough:

• 2 ½ cups all-purpose flour
• 1 teaspoon baking powder
• ½ teaspoon baking soda
• ½ teaspoon salt
• 1 cup (2 sticks) unsalted butter, softened
• ¾ cup granulated sugar
• ¾ cup packed light brown sugar
• 2 large eggs
• 1 teaspoon vanilla extract

For the Pineapple Topping:

• ½ cup (1 stick) unsalted butter
• ¾ cup packed light brown sugar
• 1 (20 ounce) can pineapple slices, drained well and patted dry
• Maraschino cherries, halved (optional)

Instructions

1. Prepare the Pineapple Topping: Melt ½ cup unsalted butter in a medium saucepan over medium heat until fully melted but not browned. Stir in ¾ cup packed light brown sugar and continue stirring constantly until sugar dissolves and mixture is smooth and glossy, about 2-3 minutes.
2. Prepare the Baking Sheet: Line a large baking sheet with parchment paper. Pour the caramelized brown sugar mixture evenly onto the parchment and spread into a thin, even layer. Arrange drained pineapple slices on top of caramel layer, spacing about 2 inches apart. Place halved maraschino cherries in the center of each pineapple slice if desired.
3. Make the Cookie Dough: In a medium bowl, whisk together flour, baking powder, baking soda, and salt. In a large bowl or a stand mixer bowl, cream softened butter, granulated sugar, and brown sugar until light and fluffy, about 3-5 minutes. Beat in eggs one at a time ensuring full incorporation, then add vanilla extract. Gradually add dry ingredients and mix on low speed just until combined, avoiding overmixing.
4. Chill the Dough: Wrap the dough in plastic wrap and chill in the refrigerator for at least 30 minutes to prevent spreading during baking.
5. Assemble Cookies: Preheat oven to 375°F (190°C) with the rack in the center position. Using a cookie scoop (about 1.5 tablespoons), portion dough and gently flatten each scoop into a disc. Place each dough disc on top of a pineapple slice on the prepared baking sheet and press gently to adhere.
6. Bake: Bake the cookies for 10-12 minutes or until cookie edges are lightly golden brown. Watch carefully to avoid overbaking.
7. Cool and Invert: Remove from oven and cool on the baking sheet for 5 minutes to allow caramel to set. Carefully invert the cookies onto a wire rack using a thin spatula to release any sticking cookies. Let cool completely before serving.

Notes

• Drain the pineapple thoroughly to prevent soggy cookies.
• Do not overbake to maintain soft, tender cookies.
• Use softened butter for better creaming and fluffy cookie texture.
• Chilling the dough is essential to minimize spreading during baking.
• Always use parchment paper for easy removal of sticky caramel topping.
• Try variations by adding cinnamon or nutmeg to dough or substituting different fruits for topping.
• Store cooled cookies in an airtight container at room temperature for up to 3 days.

Keywords: pineapple upside down cookies, sugar cookies, caramelized pineapple, dessert cookies, easy baking recipe, party cookies, tropical cookies