Pineapple Upside Down Sugar Cookies Recipe
Introduction
Pineapple Upside Down Sugar Cookies offer a delightful twist on a classic favorite. Each bite combines buttery sugar cookie sweetness with a juicy pineapple topping for a refreshing treat. These cookies are perfect for sharing at gatherings or enjoying as a tropical snack.

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
- For extra flavor, try adding a pinch of cinnamon or nutmeg to the dough.
- Use fresh pineapple slices for a more natural texture, but be sure to pat dry to avoid sogginess.
- Swap granulated sugar on top with brown sugar for a richer caramel-like finish.
Storage
Store the cookies in an airtight container at room temperature for up to 3 days. For longer storage, keep them refrigerated for up to a week or freeze for up to 2 months. Reheat in a warm oven for a few minutes to restore freshness.
How to Serve
Serve this delicious recipe with your favorite sides.
FAQs
Can I make these cookies gluten-free?
Yes, simply substitute the all-purpose flour with an equal amount of a gluten-free baking blend. Make sure the blend contains xanthan gum or another binder to maintain texture.
How do I prevent soggy cookies from the pineapple rings?
Thoroughly drain the pineapple rings and pat them dry with paper towels before placing them on the dough. This helps reduce excess moisture and keeps the cookies crisp.
PrintPineapple Upside Down Sugar Cookies Recipe
These Pineapple Upside Down Sugar Cookies combine the classic tropical flavor of pineapple upside-down cake with the simplicity of sugar cookies. Each bite delights with buttery, soft cookie dough crowned by a caramelized pineapple ring, making them perfect for parties or a sweet everyday treat.
- Prep Time: 15 minutes
- Cook Time: 13 minutes
- Total Time: 28 minutes
- Yield: 24 servings 1x
- Category: Dessert
- Method: Baking
- Cuisine: American
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 granulated sugar for sprinkling
Instructions
- Preheat Oven: Preheat your oven to 350°F (180°C) and line baking trays with parchment paper to prevent sticking and ensure even baking.
- Cream Butter and Sugar: In a large bowl, cream the softened unsalted butter and granulated sugar together using a mixer or by hand until the mixture is light and fluffy, about 2-3 minutes, which creates the perfect base for the cookie dough.
- Add Egg and Vanilla: Beat in the large egg and vanilla extract to the creamed mixture until fully combined, providing flavor and structure to the dough.
- Mix Dry Ingredients: In a separate bowl, whisk together the all-purpose flour, baking soda, and salt to ensure even distribution of the leavening agent and seasoning.
- Combine Wet and Dry Ingredients: Gradually add the dry ingredients to the wet mixture, stirring gently until a soft and cohesive cookie dough forms without overmixing.
- Portion Dough: Scoop about 2 tablespoons of dough per cookie and place each mound onto the prepared baking trays, making sure to leave space between them for spreading.
- Add Pineapple Topping: Press one well-drained pineapple ring gently into the top of each dough mound, flattening the cookie slightly to hold the topping securely.
- Sprinkle Sugar: Generously sprinkle 2 tablespoons of additional granulated sugar over the pineapple rings to add sparkle and eventual caramelization during baking.
- Bake Cookies: Bake the cookies in the preheated oven for 11-13 minutes or until the edges turn golden brown and the centers are set, ensuring a perfect balance of softness and structure.
- Cool: Allow the cookies to cool on the baking tray for a few minutes to firm up before transferring them to a wire rack to cool completely, which helps preserve their texture and prevents sogginess.
Notes
- Ensure pineapple rings are well-drained to avoid soggy cookie bottoms.
- You can use a gluten-free flour blend to make this recipe gluten-free.
- The vanilla extract is optional but adds a richer flavor to the cookies.
- Make sure not to overmix the dough to keep cookies tender.
- For extra caramelization, try broiling the cookies for 1-2 minutes after baking but watch closely to prevent burning.
Keywords: pineapple upside down cookies, sugar cookies, pineapple cookies, fruity sugar cookies, dessert, holiday baking

