If you are craving a delightful twist on a classic sweet treat, look no further than this Pineapple Upside Sugar Cookies Recipe. Imagine soft, buttery sugar cookies infused with juicy crushed pineapple and topped with a vibrant maraschino cherry and a sprinkle of brown sugar that caramelizes to perfection. Every bite bursts with a tropical surprise, mixing the best textures and flavors to make cookie time something truly special. This recipe is a joyful celebration of fruit and sweetness, perfect to brighten any day or impress your friends and family with a unique homemade delight.

Ingredients You’ll Need
These ingredients are simple pantry staples, yet each plays a crucial role in creating the perfect balance of flavor and texture for the Pineapple Upside Sugar Cookies Recipe. From the rich butter that ensures a tender crumb to the tangy crushed pineapple adding moisture and zing, every component brings something special to the mix.
- Unsalted butter: Provides a creamy base and delicate richness to the cookie dough.
- Granulated sugar: Sweetens the dough and helps create a light, fluffy texture when creamed with butter.
- Egg: Binds the ingredients together while lending structure and tenderness.
- Vanilla extract: Adds a warm, aromatic layer to complement the pineapple’s brightness.
- All-purpose flour: The foundation of the cookies, balancing moisture and giving shape.
- Baking powder: Ensures a subtle rise, making the cookies soft yet gently fluffy.
- Salt: Enhances all the flavors and balances the sweetness perfectly.
- Crushed pineapple (drained): Infuses juicy tropical moisture and a lovely fruity flavor into every bite.
- Maraschino cherries: Gorgeous, sweet decorations nestled on each cookie’s crown.
- Brown sugar: Sprinkled on top to add a delightful caramelized crunch and rich sweetness.
How to Make Pineapple Upside Sugar Cookies Recipe
Step 1: Preheat and prepare
Start by setting your oven to 350°F (175°C) so it reaches the perfect baking temperature right when your dough is ready. Line a baking sheet with parchment paper to ensure your cookies bake evenly and don’t stick – a simple trick that always makes cleanup easier.
Step 2: Cream the butter and sugar
In a mixing bowl, beat the softened butter and granulated sugar until light and fluffy. This step is crucial because it incorporates air into the dough, giving your cookies a tender, melt-in-your-mouth texture.
Step 3: Add egg and vanilla
Next, mix in the egg and vanilla extract thoroughly. The egg will help bind all the ingredients together, while the vanilla provides a rich, fragrant background flavor that pairs brilliantly with the pineapple.
Step 4: Combine dry ingredients
Whisk the flour, baking powder, and salt together in a separate bowl. This ensures even distribution of the leavening agents and prevents any clumps of salt, giving your cookies a perfectly balanced flavor and texture.
Step 5: Mix dry ingredients into wet
Gradually add the dry mixture into the wet ingredients, stirring gently until everything is well combined. This careful mixing keeps the dough tender without overworking the gluten in the flour.
Step 6: Fold in crushed pineapple
Gently fold the drained crushed pineapple into the cookie dough. The pineapple not only adds moistness but also a subtle tanginess that elevates these cookies far beyond the ordinary.
Step 7: Shape dough and decorate
Use a tablespoon to scoop dough balls onto your prepared baking sheet, spacing them to allow for spreading. Press a halved maraschino cherry into the center of each cookie, then sprinkle a pinch of brown sugar on top. This combination will create an irresistible caramelized topping as the cookies bake.
Step 8: Bake to perfection
Bake for 10-12 minutes until the cookies’ edges turn lightly golden. This timing ensures they remain soft and chewy in the center with just the right amount of crispness on the edges.
Step 9: Cool and enjoy
Let the cookies cool on the baking sheet for a few minutes before transferring them to a wire rack to cool completely. This cooling time helps them set perfectly while preserving their tender texture.
How to Serve Pineapple Upside Sugar Cookies Recipe

Garnishes
For an extra touch, dust your cookies lightly with powdered sugar or drizzle a simple glaze made from powdered sugar and a few drops of pineapple juice. Fresh mint leaves also add a refreshing hint and vibrant color when serving these alongside your cookies.
Side Dishes
Pair these tropical-inspired cookies with a scoop of vanilla ice cream or coconut sorbet for an indulgent treat. A hot cup of tea or even a chilled glass of pineapple juice makes an excellent companion, enhancing the fruity, sweet flavors.
Creative Ways to Present
Arrange the cookies on a tropical-themed platter adorned with pineapple slices and cherries for a visually stunning dessert display. You can also sandwich two cookies together with cream cheese frosting or pineapple jam for a fun and delicious twist on this Pineapple Upside Sugar Cookies Recipe.
Make Ahead and Storage
Storing Leftovers
Store your leftover Pineapple Upside Sugar Cookies in an airtight container at room temperature. They should stay fresh and soft for up to a week, so you can enjoy these tropical delights over several days without losing any flavor or texture.
Freezing
If you want to keep these cookies longer, freeze them in a sealed container with parchment paper between layers to prevent sticking. They can be frozen for up to 3 months, making it easy to enjoy a sunny treat any time you want.
Reheating
To refresh frozen cookies, thaw them at room temperature, then warm briefly in a low oven (about 300°F) for 5 minutes. This will revive their soft texture and bring back that freshly baked warmth you love.
FAQs
Can I use fresh pineapple instead of canned crushed pineapple?
Absolutely! Just make sure to finely chop fresh pineapple and drain it well to avoid adding too much moisture, which can affect the cookie’s texture. Fresh pineapple will offer a brighter, juicier bite.
What if I don’t have maraschino cherries?
If maraschino cherries aren’t available, you can substitute with small pieces of dried fruit, fresh berries, or even colorful candy pieces for decoration and a pop of flavor.
Are these cookies gluten-free?
The recipe calls for all-purpose flour, which contains gluten. To make a gluten-free version, substitute with a gluten-free flour blend that measures cup-for-cup, but be mindful you may need to adjust baking time slightly.
Can I make these cookies vegan?
With some modifications like using vegan butter, a flax egg, and replacing maraschino cherries with vegan-friendly options, you can adapt this recipe to be vegan, keeping the tropical sweetness intact.
How do I prevent the cookies from spreading too much?
Make sure your butter is softened but not melted, and chill the dough briefly before baking if your kitchen is warm. This helps the cookies hold their shape and keeps the cherry nicely centered.
Final Thoughts
Sharing this Pineapple Upside Sugar Cookies Recipe feels like handing over a little slice of tropical magic wrapped in a warm, buttery cookie. Its unique combination of flavors and inviting textures will quickly become a staple, whether for a casual snack or a special occasion. Trust me, once you try these, you’ll find countless reasons to bake them over and over. So go ahead, give these cookies a whirl and watch everyone’s faces light up with every bite!
Print
Pineapple Upside Sugar Cookies Recipe
- Prep Time: 15 minutes
- Cook Time: 12 minutes
- Total Time: 27 minutes
- Yield: 24 cookies
- Category: Dessert
- Method: Baking
- Cuisine: American
- Diet: Vegetarian
Description
These Pineapple Upside Sugar Cookies are a delightful twist on classic sugar cookies, featuring crushed pineapple and a sweet maraschino cherry topping. Perfectly soft and subtly tropical, these cookies are bursting with flavor and topped with a sprinkle of brown sugar for extra sweetness and a slight crunch. Ideal for parties, holiday baking, or any time you want a fruity, cheerful treat.
Ingredients
Cookie Dough
- 1 cup unsalted butter, softened
- 1 cup granulated sugar
- 1 egg
- 1 teaspoon vanilla extract
- 2 1/2 cups all-purpose flour
- 1/2 teaspoon baking powder
- 1/4 teaspoon salt
- 1/2 cup crushed pineapple, drained
Topping
- Maraschino cherries, halved
- Brown sugar for sprinkling
Instructions
- Preheat the oven: Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper to prevent sticking and ensure even baking.
- Cream butter and sugar: In a mixing bowl, use a hand or stand mixer to cream together the softened butter and granulated sugar until the mixture is light and fluffy, which helps create the perfect cookie texture.
- Add egg and vanilla: Beat in the egg and vanilla extract until fully combined, which adds moisture and enhances flavor.
- Mix dry ingredients: In a separate bowl, whisk together the all-purpose flour, baking powder, and salt thoroughly to ensure even distribution of leavening agents and seasoning.
- Combine wet and dry ingredients: Gradually add the dry ingredient mixture to the wet ingredients, mixing until just combined without overmixing to keep the cookies tender.
- Fold in pineapple: Gently fold in the drained crushed pineapple, being careful not to overwork the dough, to add a subtle fruity moisture.
- Shape cookies: Scoop tablespoon-sized balls of dough onto the prepared baking sheet, spacing them about 2 inches apart to allow for spreading.
- Add cherry and sugar topping: Press a halved maraschino cherry into the center of each cookie and sprinkle a pinch of brown sugar over the top for extra sweetness and texture.
- Bake the cookies: Bake in the preheated oven for 10-12 minutes, or until the edges turn a light golden brown, indicating they are done but still soft inside.
- Cool the cookies: Allow the cookies to cool on the baking sheet for a few minutes to set before transferring carefully to a wire rack to cool completely, preventing breakage.
Notes
- Ensure pineapple is well drained to avoid overly wet dough.
- Do not overmix the dough after adding flour to maintain a tender texture.
- Use parchment paper or a silicone baking mat for easy release.
- Cookies are best enjoyed within 2-3 days stored in an airtight container at room temperature.
- You can substitute maraschino cherries with fresh cherries or dried cranberries as a variation.