These Pineapple Upside Sugar Cookies turn the nostalgic charm of pineapple upside-down cake into buttery, fruit-topped cookies that are as beautiful as they are delicious. I love how the soft sugar cookie base pairs perfectly with caramelized pineapple rings, creating a tropical, bakery-worthy treat that’s ideal for bake sales, parties, or simply a sweet moment at home. Every bite delivers that balance of rich cookie dough and tangy-sweet fruit, with golden edges and a stunning presentation.

Why You’ll Love This Recipe

• I get all the flavors of classic pineapple upside-down cake in a neat, portable cookie.

• The pineapple rings caramelize beautifully while baking, creating a golden, impressive look with zero effort.

• I only need simple pantry ingredients plus canned pineapple, which makes this super convenient.

• These cookies are individually portioned, which makes serving and storing much easier.

• They’re nostalgic, flavorful, and a crowd favorite no matter where I bring them.

Ingredients

(Here’s a tip: Check out the full list of ingredients and measurements in the recipe card below.)

For The Cookie Dough Base:

• 1 cup unsalted butter, softened to room temperature – this ensures proper creaming and a tender, rich texture

• 1 cup granulated sugar – provides sweetness and contributes to golden cookie edges

• 1 large egg – binds everything together and adds richness

• 1 teaspoon pure vanilla extract – enhances flavor without overpowering the pineapple

For The Dry Ingredients:

• 2 1/2 cups all-purpose flour – gives the cookies their structure so they hold the pineapple rings

• 1/2 teaspoon baking soda – adds slight lift and helps achieve a soft, chewy interior

• 1/4 teaspoon fine salt – balances the sweetness and boosts all the other flavors

For The Pineapple Topping:

• 10 to 12 canned pineapple rings – well-drained and patted completely dry with paper towels to prevent sogginess and encourage caramelization

• Extra granulated sugar – for sprinkling over the pineapple rings to add sparkle and extra caramelization

Directions

1. I start by preheating my oven to 350°F (175°C) and lining two baking sheets with parchment paper. This helps the cookies release easily and makes cleanup quick.

2. In a large mixing bowl, I cream together the softened butter and sugar using a hand or stand mixer for about 3 to 4 minutes, until the mixture is pale, light, and fluffy. This step is key to creating tender cookies.

3. I add the egg and vanilla extract to the creamed butter and sugar, then beat until fully combined and smooth.

4. In a separate bowl, I whisk together the flour, baking soda, and salt. This ensures even distribution of the leavening agents.

5. I gradually add the dry ingredients to the wet mixture, mixing just until a soft dough forms. I avoid overmixing, as that can make the cookies tough instead of tender.

6. Using about 1 1/2 tablespoons of dough per cookie, I roll the dough into balls and place them on the prepared baking sheets. I gently flatten each ball into a disk so the pineapple ring can sit securely on top.

7. I press one well-dried pineapple ring into the top of each flattened dough disk, pressing gently but firmly so it adheres without pushing through the dough.

8. I sprinkle a small pinch of granulated sugar over each pineapple ring for added shine and caramelization during baking.

9. I bake the cookies for 12 to 14 minutes, or until the edges are golden and the cookies look set. I avoid overbaking to keep them soft and tender.

10. I let the cookies cool on the baking sheets for 5 minutes, then transfer them to a wire rack to cool completely before storing or serving.

Servings And Timing

• Servings: Makes 10 to 12 large cookies

• Preparation Time: 20 minutes

• Baking Time: 12 to 14 minutes

• Total Time: About 34 minutes

• Skill Level: Moderate

• Cuisine Type: American

• Dietary Option: Vegetarian

Variations

• I like to add sweetened shredded coconut to the dough for extra tropical flavor.

• Swapping white sugar for light brown sugar gives a deeper, richer taste.

• For a fun twist, I sometimes use pineapple tidbits instead of rings and make mini cookies.

• A maraschino cherry in the center of each ring gives that classic upside-down cake look and extra pop of color.

• Adding a pinch of cinnamon to the sugar topping creates a warm, spiced variation.

Storage/Reheating

Once the cookies are fully cooled, I store them in an airtight container at room temperature. I separate layers with parchment paper to prevent sticking. They keep well for up to 4 days, though I find the texture is best within the first 2 days.

I don’t reheat these cookies, since the pineapple can turn rubbery. They’re best enjoyed at room temperature, where the flavors and textures shine.

FAQs

Why Do I Need To Pat The Pineapple Rings Dry?

I always pat the pineapple rings dry before baking because extra moisture can cause the cookies to become soggy and prevent proper caramelization on top.

Can I Use Fresh Pineapple Instead Of Canned?

Yes, I can use fresh pineapple as long as I slice it into 1/4-inch thick rings and pat it very dry. I find canned pineapple more consistent in size and texture for baking.

How Do I Know When The Cookies Are Done?

I look for lightly golden edges and set centers. When I gently touch the middle, it should feel firm but not hard. They continue to firm up as they cool on the baking sheet.

Can I Add Cherries Like The Classic Cake?

Absolutely. I often place a maraschino cherry in the center of each pineapple ring before baking for that nostalgic look and a sweet burst of flavor.

Can I Make The Dough Ahead Of Time?

Yes, I make the dough ahead and refrigerate it for up to 2 days. Before shaping and baking, I let it come to room temperature so it’s easier to work with.

Conclusion

Pineapple Upside Sugar Cookies are my go-to when I want to serve something that feels special but doesn’t require complicated steps. They combine the timeless flavors of a classic dessert with the ease and charm of a handheld cookie. From the golden pineapple topping to the rich, buttery base, every bite is a delightful balance of texture and flavor. Whether I’m making them for a summer gathering or just a weekday pick-me-up, they never last long in the cookie jar.