Introduction

Pineapple Upside Down Sugar Cookies are a fun, creative twist on the classic pineapple upside down cake—reimagined into soft, buttery cookies that are just as eye-catching as they are delicious. These cookies combine tender sugar cookie bases with caramelized brown sugar, juicy pineapple, and bright maraschino cherries, delivering all the nostalgic flavors of the beloved dessert in an easy-to-serve handheld treat.

What makes these cookies special is the contrast of textures and flavors. The sugar cookie base is soft and slightly chewy, while the pineapple topping adds juiciness and tropical sweetness. The brown sugar melts during baking, creating a lightly caramelized glaze that soaks into the cookie beneath, adding richness and depth.

These cookies are perfect for summer gatherings, holiday dessert trays, potlucks, bake sales, and themed parties. They look impressive but are surprisingly simple to make, using pantry staples and basic techniques. Because each cookie is individually topped, they bake evenly and are easy to portion and serve.

This detailed recipe will walk you through every step to ensure your Pineapple Upside Down Sugar Cookies come out soft, flavorful, and beautifully topped every time. You’ll also find variations, tips, serving ideas, and FAQs to help you master this unique dessert.

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Ingredients:

For the Sugar Cookies

• 1 cup (226 g) unsalted butter, softened
• 1 cup granulated sugar
• 1 large egg
• 1 teaspoon vanilla extract
• 2 1/2 cups all-purpose flour
• 1/2 teaspoon baking powder
• 1/4 teaspoon salt

For the Topping

• 1/2 cup packed brown sugar
• 1/4 cup unsalted butter, melted
• 1 can pineapple slices or chunks, well drained
• Maraschino cherries, halved

Preparation :

Step 1: Prepare the Pineapple Topping

In a small bowl, mix the brown sugar and melted butter until combined. Set aside. Pat pineapple completely dry with paper towels to prevent excess moisture.

Step 2: Cream Butter and Sugar

In a large mixing bowl, beat softened butter and granulated sugar together until light and fluffy.

Step 3: Add Egg and Vanilla

Mix in the egg and vanilla extract until fully incorporated.

Step 4: Combine Dry Ingredients

In a separate bowl, whisk together flour, baking powder, and salt.

Step 5: Form the Dough

Gradually add the dry ingredients to the wet mixture, mixing just until combined. Do not overmix.

Step 6: Chill the Dough

Cover and refrigerate dough for 30 minutes. Chilling helps cookies hold their shape.

Step 7: Preheat and Prepare Baking Sheets

Preheat oven to 350°F (175°C). Line baking sheets with parchment paper.

Step 8: Add the Topping

Place 1 teaspoon of brown sugar mixture on each cookie spot. Add a pineapple piece and top with a cherry half.

Step 9: Add Cookie Dough

Scoop about 2 tablespoons of cookie dough and gently place it on top of each pineapple topping. Lightly flatten.

Step 10: Bake

Bake for 12–15 minutes, until edges are set and bottoms are lightly golden.

Step 11: Flip and Cool

Allow cookies to cool for 5 minutes, then carefully flip them pineapple-side up. Let cool completely.

Variation

🍍 1. Coconut Pineapple Cookies
Add shredded coconut to the cookie dough for tropical flair.

🍒 2. Extra Cherry Cookies
Use two cherry halves per cookie for added sweetness.

🍯 3. Honey Pineapple Cookies
Replace brown sugar with honey for a floral note.

🍋 4. Pineapple Lemon Cookies
Add lemon zest to brighten the flavor.

🧁 5. Mini Pineapple Upside Down Cookies
Make smaller versions using mini pineapple chunks.

COOKING Note :

• Drain pineapple thoroughly to avoid soggy cookies.
• Flip cookies while warm to prevent sticking.
• Do not overbake—the cookies should remain soft.
• Use parchment paper for easy release.

Serving Suggestions :

• Serve at summer parties or BBQs
• Add to tropical-themed dessert tables
• Pair with vanilla ice cream
• Serve with iced tea or lemonade
• Package individually for bake sales

Tips :

• Use room-temperature butter for smooth dough.
• Pat fruit dry before baking.
• Chill dough if cookies spread too much.
• Use a spatula to flip cookies gently.
• Store cookies in a single layer if possible.

Prep Time:

25 minutes

Cooking Time:

15 minutes

Total Time:

40 minutes (plus chilling)

Nutritional Information :

(Approximate per cookie)
Calories: ~210
Protein: ~2 g
Sodium: ~130 mg

FAQs

1. Can I use fresh pineapple?

Yes, but chop finely and remove excess juice.

2. Why did my cookies stick?

Flip them while still warm and use parchment paper.

3. Can I make these ahead of time?

Yes, they taste great the next day.

4. Do these cookies stay soft?

Yes, due to the sugar cookie base.

5. How should I store them?

Store in an airtight container for up to 3 days.

Conclusion

Pineapple Upside Down Sugar Cookies bring together classic comfort and tropical flair in one unforgettable dessert. With their soft sugar cookie base, caramelized brown sugar topping, and vibrant fruit finish, they’re as beautiful as they are delicious. Perfect for parties, holidays, or everyday baking, these cookies are guaranteed to impress anyone who takes a bite.