Pineapple Upside Down Sugar Cookies That Delight Every Bite Recipe
Introduction
Pineapple upside down sugar cookies offer a delightful twist on a classic favorite. Combining the sweet, tangy flavor of pineapple with soft, buttery cookie dough, these treats are perfect for any occasion. They’re easy to make and sure to impress with every bite.

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
- Step 1: Preheat your oven to 350°F (180°C) and line your baking trays with parchment paper.
- Step 2: Cream the softened unsalted butter and granulated sugar together until light and fluffy, about 2-3 minutes.
- Step 3: Add the large egg and vanilla extract, beating well until combined.
- Step 4: Whisk together the all-purpose flour, baking soda, and salt in a separate bowl, then gradually mix into the wet mixture until a soft dough forms.
- Step 5: Scoop 2 tablespoons of dough for each cookie and place on the prepared trays, leaving space between each.
- Step 6: Press a pineapple ring gently into each dough mound, flattening slightly.
- Step 7: Sprinkle additional sugar generously on top of the pineapple rings.
- Step 8: Bake for 11-13 minutes, or until edges are golden and centers are set.
- Step 9: Cool the cookies on the tray for a few minutes before transferring to a wire rack for complete cooling.
Tips & Variations
- Use fresh pineapple rings for a juicier topping and a fresher taste.
- For extra flavor, add a pinch of cinnamon or nutmeg to the dough mixture.
- Substitute the all-purpose flour with gluten-free blend to make the cookies gluten-free.
- If you prefer smaller cookies, reduce the dough scoop size and adjust baking time accordingly.
Storage
Store the cookies in an airtight container at room temperature for up to 4 days. To keep them soft, place a slice of bread in the container. They can also be refrigerated for up to a week. Reheat gently in the microwave for 10-15 seconds to bring back softness.
How to Serve

Serve this delicious recipe with your favorite sides.
FAQs
Can I use fresh pineapple instead of canned?
Yes, fresh pineapple works well. Make sure to slice the rings thinly and drain any excess juice to avoid soggy dough.
How do I prevent the cookies from spreading too much?
Chill the dough for about 30 minutes before baking. Also, avoid pressing the pineapple rings too deeply into the dough to maintain shape.
Print
Pineapple Upside Down Sugar Cookies That Delight Every Bite Recipe
- Total Time: 27 minutes
- Yield: 24 cookies 1x
Description
These Pineapple Upside Down Sugar Cookies are a delightful twist on the classic pineapple upside down cake, combining soft, buttery sugar cookie dough with sweet, juicy pineapple rings on top. Each bite offers a perfect balance of buttery richness and tropical fruitiness, making them an irresistible treat for any occasion.
Ingredients
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
- 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.
- Cream Butter and Sugar: In a large bowl, cream the softened unsalted butter and granulated sugar together until the mixture becomes light and fluffy, approximately 2 to 3 minutes, which helps incorporate air for a tender cookie texture.
- Add Egg and Vanilla: Beat in the large egg and vanilla extract (if using) until fully incorporated, which adds moisture and flavor to the dough.
- Mix Dry Ingredients: In a separate bowl, whisk together the all-purpose flour, baking soda, and salt to evenly distribute the leavening and seasoning.
- Combine Wet and Dry: Gradually add the dry ingredients to the wet mixture, mixing until a soft, uniform dough forms without overmixing to keep the cookies tender.
- Form Cookies: Scoop about 2 tablespoons of dough per cookie and place them evenly spaced on the prepared baking trays to allow room for spreading.
- Add Pineapple Topping: Gently press a well-drained canned pineapple ring into the top of each dough mound, flattening it slightly to adhere without squashing the dough.
- Sprinkle Sugar: Generously sprinkle 2 tablespoons of additional sugar over the pineapple rings to create a caramelized sweetness during baking.
- Bake: Bake in the preheated oven for 11 to 13 minutes, or until the cookie edges turn golden and the centers are set but still soft.
- Cool: Allow the cookies to cool on the baking tray for a few minutes before transferring them to a wire rack to cool completely, which helps them firm up and prevents sogginess.
Notes
- Make sure pineapple rings are well-drained to prevent soggy cookies.
- For a gluten-free version, substitute with a gluten-free flour blend.
- Vanilla extract is optional but enhances the flavor.
- Be careful not to overbake; cookies should be golden with soft centers.
- Allow cookies to cool fully to set texture before serving.
- Prep Time: 15 minutes
- Cook Time: 12 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
Keywords: pineapple upside down cookies, sugar cookies, pineapple dessert, easy cookies, tropical cookies

