Introduction

These Pineapple Upside Sugar Cookies bring a tropical twist to a classic treat. Soft sugar cookies topped with juicy pineapple rings make for a delightful and visually appealing dessert. Perfect for summer gatherings or a fun baking project.

A stack of four round pineapple upside-down cakes sits at the center of a white plate on a white marbled surface. Each cake layer has a bright, glossy yellow pineapple slice on the top with a slightly caramelized texture shining under light, and the edges are coated with a layer of coarse sugar crystals that sparkle and add texture. The cakes are golden yellow with a soft, crumbly appearance at the sides, and two single pineapple cakes rest flat on the plate, slightly out of focus in the background. Photo taken with an iphone --ar 4:5 --v 7

Ingredients

1 cup unsalted butter, softened
1 cup granulated sugar
1 egg
1 tsp vanilla extract
2½ cups all-purpose flour
½ tsp baking soda
¼ tsp salt
10–12 canned pineapple rings, well-drained and patted dry
Additional sugar for sprinkling

Instructions

Step 1: Preheat your oven to 350°F (175°C) and line baking sheets with parchment paper.
Step 2: In a large bowl, cream together the softened butter and sugar until the mixture is light and fluffy.
Step 3: Beat in the egg and vanilla extract until well combined.
Step 4: In a separate bowl, whisk together the flour, baking soda, and salt. Gradually add this dry mixture to the butter mixture, stirring to form a soft dough.
Step 5: Roll the dough into balls about 1½ tablespoons each. Flatten them slightly and arrange on the prepared baking sheet.
Step 6: Place a pineapple ring gently on top of each dough disk, pressing down slightly to adhere.
Step 7: Sprinkle additional sugar on top of each pineapple ring to add sparkle and extra sweetness.
Step 8: Bake for 12 to 14 minutes, or until the cookie edges turn golden. Let cool on the sheet for 5 minutes, then transfer to a wire rack to cool completely.

Tips & Variations

Use fresh pineapple slices if canned aren’t available, just be sure to pat them dry to avoid soggy cookies.
For a caramelized effect, brush pineapple rings with a little melted brown sugar or honey before baking.
Add a sprinkle of cinnamon or nutmeg to the dough for a warm, spicy note.
Chill the dough briefly before baking if it feels too soft; this helps the cookies keep their shape.

Storage

Store cooled cookies in an airtight container at room temperature for up to 4 days. To keep them fresh longer, refrigerate for up to a week. Reheat gently in a low oven or microwave for a few seconds to restore softness.

How to Serve

A close-up view of a stack of four pineapple cookies placed on a white plate sitting on a white marbled surface. Each cookie has a golden-yellow color with a lightly crumbly texture covered in sugar crystals around the edges. The top cookie is decorated with a thin, translucent slice of pineapple with visible segments radiating from the center, which is sprinkled with coarse sugar crystals that sparkle under the light. The cookies below have a uniform thickness and a slightly cracked surface, showing their soft inside. The photo taken with an iphone --ar 4:5 --v 7

Serve this delicious recipe with your favorite sides.

FAQs

Can I use fresh pineapple instead of canned for this recipe?

Yes, fresh pineapple works well if you slice it into rings and pat them dry thoroughly to avoid excess moisture, which can affect the cookie texture.

How do I prevent the pineapple from making the cookies soggy?

Make sure to drain canned pineapple well and pat dry before placing on the dough. Sprinkling sugar on top helps create a slight barrier as well.

Pineapple Upside Sugar Cookies Recipe

Print Recipe

★★★★★

4.5 from 93 reviews

Delightfully sweet and buttery Pineapple Upside Sugar Cookies combine classic sugar cookies with pineapple rings for a refreshing tropical twist. Soft, golden cookies topped with juicy, caramelized pineapple rings make an eye-catching and delicious treat perfect for snacks or dessert.

Author: Stella
Prep Time: 15 minutes
Cook Time: 14 minutes
Total Time: 29 minutes
Yield: 10–12 cookies 1x
Category: Dessert
Method: Baking
Cuisine: American
Diet: Vegetarian

Ingredients

Scale

Cookie Dough

1 cup unsalted butter, softened
1 cup granulated sugar
1 egg
1 tsp vanilla extract
2½ cups all-purpose flour
½ tsp baking soda
¼ tsp salt

Toppings

10–12 canned pineapple rings, well-drained and patted dry
Additional sugar for sprinkling

Instructions

Preheat Oven: Preheat your oven to 350°F (175°C) and line baking sheets with parchment paper to prevent sticking and for easy cleanup.
Cream Butter and Sugar: In a large bowl, cream together the softened unsalted butter and granulated sugar until the mixture is light, fluffy, and pale in color, ensuring a tender cookie texture.
Add Egg and Vanilla: Beat in the egg and vanilla extract until the ingredients are thoroughly combined, adding moisture and flavor to the dough.
Combine Dry Ingredients: In a separate bowl, whisk together the all-purpose flour, baking soda, and salt. Gradually add this dry mixture to the butter mixture, stirring until a soft dough forms. Be careful not to overmix.
Shape Cookies: Roll the dough into approximately 1½ tablespoon-sized balls. Place them on the prepared baking sheets, flattening each slightly to create a disk shape for even baking.
Add Pineapple Rings: Gently press one canned pineapple ring onto the top of each flattened dough disk, ensuring it adheres well but does not sink completely.
Sprinkle Sugar: Sprinkle additional granulated sugar on top of the pineapple rings to add sparkle and a sweet crunchy crust after baking.
Bake Cookies: Bake the cookies in the preheated oven for 12 to 14 minutes, or until the edges turn golden brown. This ensures the cookies are fully cooked but remain soft.
Cool and Serve: Allow the cookies to cool on the baking sheet for 5 minutes after removing from the oven, then transfer them to a wire rack to cool completely before serving.

Notes

Ensure pineapple rings are well-drained and patted dry to prevent soggy cookies.
For a more intense pineapple flavor, lightly caramelize the pineapple rings in a skillet before pressing them onto the cookie dough.
Store cookies in an airtight container at room temperature for up to 3 days to maintain freshness.
For a festive touch, add a sprinkle of cinnamon or a drizzle of honey on top before baking.

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