Pineapple Upside Down Sugar Cookies That Delight Every Bite Recipe

Introduction

Pineapple Upside Down Sugar Cookies offer a delightful twist on a classic dessert. With a soft, buttery base topped by juicy pineapple rings and a sprinkle of sugar, each bite is a perfect balance of sweet and tangy. They’re easy to make and sure to impress your family and friends.

Ingredients

• 1 cup unsalted butter (softened)
• 1 cup granulated sugar
• 1 large egg
• 1 teaspoon vanilla extract (optional)
• 2 cups all-purpose flour (or gluten-free blend)
• 1 teaspoon baking soda
• 1/2 teaspoon salt
• 1 can canned pineapple rings (well-drained)
• 2 tablespoons additional sugar for sprinkling

Instructions

1. Step 1: Preheat your oven to 350°F (180°C) and line your baking trays with parchment paper.
2. Step 2: Cream the softened unsalted butter and granulated sugar together until light and fluffy, about 2-3 minutes.
3. Step 3: Add the large egg and vanilla extract, beating well until combined.
4. Step 4: In a separate bowl, whisk together the all-purpose flour, baking soda, and salt.
5. Step 5: Gradually mix the dry ingredients into the wet mixture until a soft dough forms.
6. Step 6: Scoop 2 tablespoons of dough for each cookie and place on the prepared trays, leaving space between each.
7. Step 7: Gently press a pineapple ring into each dough mound, flattening slightly.
8. Step 8: Sprinkle additional sugar generously on top of the pineapple rings.
9. Step 9: Bake for 11-13 minutes, or until edges are golden and centers are set.
10. Step 10: Cool the cookies on the tray for a few minutes before transferring to a wire rack to cool completely.

Tips & Variations

• For extra flavor, try adding a pinch of cinnamon or nutmeg to the dough.
• Use fresh pineapple rings if available—just be sure to drain them well to avoid soggy cookies.
• Swap granulated sugar on top for brown sugar to add a caramelized touch.
• If avoiding eggs, substitute with a flax egg (1 tablespoon ground flaxseed mixed with 3 tablespoons water) and adjust baking time slightly.

Storage

Store the cookies in an airtight container at room temperature for up to 4 days. For longer storage, keep them in the refrigerator for up to a week. To reheat, warm briefly in the microwave or oven to restore their soft texture.

How to Serve

Serve this delicious recipe with your favorite sides.

FAQs

Can I use fresh pineapple instead of canned?

Yes, fresh pineapple rings can be used but make sure they are well-drained and patted dry to prevent excess moisture from affecting the cookie texture.

How do I make these cookies gluten-free?

Simply substitute the all-purpose flour with a gluten-free flour blend measured cup-for-cup. Ensure the blend includes xanthan gum or add a small amount for best results.

Pineapple Upside Down Sugar Cookies That Delight Every Bite Recipe

Print Recipe

★★★★★

4.6 from 95 reviews

These Pineapple Upside Down Sugar Cookies combine the classic flavors of pineapple upside down cake with the simplicity of sugar cookies. Soft, buttery dough is topped with juicy pineapple rings and a sprinkle of sugar, resulting in a delightful, fruity twist on a traditional cookie that’s perfect for any occasion.

• Author: Anna
• Prep Time: 15 minutes
• Cook Time: 12 minutes
• Total Time: 27 minutes
• Yield: 24 cookies 1x
• Category: Dessert
• Method: Baking
• Cuisine: American
• Diet: Vegetarian

Ingredients

Scale 1x2x3x

Cookie Dough

• 1 cup unsalted butter (softened)
• 1 cup granulated sugar
• 1 large egg
• 1 teaspoon vanilla extract (optional)
• 2 cups all-purpose flour (or gluten-free blend)
• 1 teaspoon baking soda
• 1/2 teaspoon salt

Topping

• 1 can canned pineapple rings (well-drained)
• 2 tablespoons additional sugar for sprinkling

Instructions

1. Preheat Oven: Preheat your oven to 350°F (180°C) and line your baking trays with parchment paper to prevent sticking and ensure easy cleanup.
2. Cream Butter and Sugar: In a large bowl, cream the softened unsalted butter and granulated sugar together until the mixture is light and fluffy, which usually takes about 2-3 minutes using a hand or stand mixer.
3. Add Egg and Vanilla: Beat in the large egg and vanilla extract (if using) until the ingredients are fully combined, ensuring an even texture.
4. Combine Dry Ingredients: In a separate bowl, whisk together the all-purpose flour, baking soda, and salt to distribute the leavening agents evenly.
5. Mix Dry and Wet Ingredients: Gradually add the dry ingredient mixture into the wet mixture, stirring until a soft dough forms without overmixing.
6. Portion the Dough: Scoop approximately 2 tablespoons of dough for each cookie and place them spaced apart on the prepared baking trays to allow for spreading during baking.
7. Add Pineapple Rings: Gently press one well-drained pineapple ring into the top of each dough mound, flattening the dough slightly to adhere the pineapple.
8. Sprinkle Sugar: Generously sprinkle 2 tablespoons of additional granulated sugar over the pineapple rings to create a caramelized sweetness when baked.
9. Bake: Place the trays in the preheated oven and bake for 11-13 minutes, or until the cookie edges turn golden and the centers are set without being overly firm.
10. Cool: Allow the cookies to cool on the baking trays for a few minutes before transferring them to wire racks for complete cooling, which helps them set perfectly.

Notes

• Make sure the pineapple rings are well-drained to prevent the dough from becoming soggy.
• The vanilla extract is optional but adds a lovely depth of flavor to the cookies.
• You can substitute all-purpose flour with a gluten-free flour blend to make these cookies gluten-free.
• Store cooled cookies in an airtight container at room temperature for up to 5 days.
• For extra caramelization, broil for 1-2 minutes after baking, watching carefully to avoid burning.

Keywords: pineapple upside down cookies, pineapple sugar cookies, pineapple cookies, upside down dessert, sweet cookies, fruit cookies, easy cookie recipe