Pineapple Upside Down Sugar Cookies are a fun twist on the classic pineapple upside-down cake. These soft sugar cookies are topped with caramelized pineapple rings and bright maraschino cherries, creating a sweet, buttery cookie with a tropical flavor and beautiful presentation.

This Pineapple Upside Down Sugar Cookies recipe is perfect for summer desserts, parties, or when you want a unique cookie that’s both fruity and delicious.

Why You’ll Love Pineapple Upside Down Sugar Cookies

Tropical pineapple flavor
Soft and buttery sugar cookie base
Caramelized pineapple topping
Beautiful presentation
Perfect for parties and gatherings
Easy homemade dessert

Ingredients for Pineapple Upside Down Sugar Cookies

Ingredient	Amount
All-purpose flour	2 cups
Baking powder	1 teaspoon
Salt	¼ teaspoon
Unsalted butter (softened)	¾ cup
Sugar	¾ cup
Egg	1 large
Vanilla extract	1 teaspoon

Pineapple Topping

Ingredient	Amount
Pineapple rings (cut into small pieces)	1 cup
Brown sugar	½ cup
Melted butter	3 tablespoons
Maraschino cherries (halved)	12

How to Make Pineapple Upside Down Sugar Cookies

Step 1: Preheat the Oven

Preheat the oven to 350°F (175°C).

Line a baking sheet with parchment paper.

Step 2: Prepare the Pineapple Topping

In a small bowl mix:

Brown sugar
Melted butter

Spoon a small amount onto the baking sheet for each cookie.

Place pineapple pieces and half a cherry on top.

In a bowl whisk together:

Flour
Baking powder
Salt

In another bowl beat together:

Butter
Sugar

until light and fluffy.

Add the egg and vanilla extract and mix well.

Gradually add the dry ingredients to form the dough.

Step 4: Assemble the Cookies

Place a scoop of cookie dough over each pineapple topping and gently flatten.

Step 5: Bake

Bake the Pineapple Upside Down Sugar Cookies for 12–15 minutes until golden.

Step 6: Flip the Cookies

Allow cookies to cool for a few minutes.

Carefully flip them over so the pineapple topping is on top.

Tips for the Best Pineapple Upside Down Sugar Cookies

Drain pineapple well to avoid excess moisture.
Use parchment paper for easy removal.
Do not overbake to keep cookies soft.
Serve slightly warm for the best flavor.

Variations of Pineapple Upside Down Sugar Cookies

You can customize Pineapple Upside Down Sugar Cookies easily:

Coconut pineapple cookies
Pineapple upside-down cupcakes
Pineapple cherry thumbprint cookies
Pineapple tropical sugar cookies

Storage Tips

Room Temperature

Store Pineapple Upside Down Sugar Cookies in an airtight container for up to 3 days.

Refrigerator

Store for up to 5 days.

FAQ About Pineapple Upside Down Sugar Cookies

What are Pineapple Upside Down Sugar Cookies?

Pineapple Upside Down Sugar Cookies are sugar cookies baked with caramelized pineapple and cherries on top.

Can I use fresh pineapple?

Yes, fresh pineapple works well if cut into small pieces.

Why should I flip the cookies?

Flipping reveals the caramelized pineapple topping.

Can I freeze Pineapple Upside Down Sugar Cookies?

Yes, they can be frozen for up to 2 months.

Conclusion

Pineapple Upside Down Sugar Cookies are a fun and tropical twist on classic sugar cookies. With their buttery cookie base and caramelized pineapple topping, they’re both beautiful and delicious.

Once you try these Pineapple Upside Down Sugar Cookies, they’ll quickly become a favorite fruity dessert for any occasion. 🍍🍒🍪✨

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