Sweet and buttery pineapple upside down sugar cookies with caramelized fruit topping—perfect for tropical dessert lovers and party treats.

Why You’ll Love This Recipe

Mini version of a classic: All the flavors of pineapple upside-down cake in a fun cookie form.
Perfectly portioned: Made in muffin tins for easy individual servings.

Soft sugar cookie base: Sweet, tender, and melts in your mouth.
Beautiful presentation: Caramelized fruit on top makes them look as good as they taste.
Easy to make: Simple ingredients and straightforward steps.

Great for sharing: A hit at potlucks, parties, and bake sales.
No fancy tools needed: Just a muffin tin and mixing bowls.
Kid-friendly: Both in flavor and fun to help assemble.

Customizable: Add your own twist with spices or flavored extracts.
Serve warm or cooled: Delicious at any temperature.

Ingredients

For The Cookie Dough:

1/2 cup unsalted butter, softened
1 cup granulated sugar
1 large egg

1 teaspoon vanilla extract
2 cups all-purpose flour
1/2 teaspoon baking powder

1/4 teaspoon salt

For The Topping:

1/4 cup unsalted butter, melted

1/2 cup brown sugar
12 maraschino cherries
1 cup pineapple tidbits, well-drained

Directions

Preheat the oven to 350°F (175°C). Grease a 12-cup muffin tin thoroughly.
In a small bowl, combine the melted butter and brown sugar. Spoon about 1 teaspoon of the mixture into the bottom of each muffin cup.
Place one maraschino cherry in the center of each muffin cup, then arrange a few pineapple tidbits around the cherry.

In a large bowl, cream the softened butter and granulated sugar until light and fluffy.
Beat in the egg and vanilla extract until fully incorporated.
In a separate bowl, whisk together the flour, baking powder, and salt. Gradually mix the dry ingredients into the wet mixture to form a dough.

Divide the dough into 12 equal balls, flatten each slightly, and place on top of the fruit in each muffin cup.
Bake for 18–22 minutes, or until the cookie edges are golden and set.
Allow the cookies to cool in the pan for 5–10 minutes. Run a knife around the edges and gently invert onto a wire rack or tray while still warm.

Serve warm or let cool completely.

Servings And Timing

Servings: 12 cookies
Prep time: 15 minutes

Cook time: 20 minutes
Total time: 35 minutes
Calories per serving: Approximately 210 kcal

Variations

Add cinnamon or nutmeg: For a spiced pineapple twist.
Use canned peaches or mango: A fun tropical swap for pineapple.
Add coconut flakes: Sprinkle some into the topping for extra island flavor.

Make gluten-free: Use a 1:1 gluten-free baking flour substitute.
Top with whipped cream: For an elegant dessert presentation.
Make them mini: Use a mini muffin tin for bite-sized versions.

Add almond extract: A small amount adds depth to the cookie dough.
Use dark brown sugar: For a richer, deeper caramel flavor.
Drizzle with icing: A simple powdered sugar glaze makes them extra special.

Skip the cherry: If you’re not a fan, just use pineapple tidbits.

Storage/Reheating

Storage: Store cooled cookies in an airtight container at room temperature for up to 3 days.
Refrigeration: Extend freshness by refrigerating up to 5 days.

Freezing: Freeze fully cooled cookies in a single layer, then transfer to a container for up to 2 months.
Reheating: Warm briefly in the microwave (10–15 seconds) to revive that just-baked taste.

FAQs

Can I Use Fresh Pineapple Instead Of Canned?

Yes, just be sure to dice it small and pat it dry to avoid excess moisture.

Do I Need To Grease The Muffin Tin If I Use Nonstick?

Yes, still grease well to ensure the caramelized topping releases cleanly.

Can I Use Store-Bought Sugar Cookie Dough?

You can, but homemade dough offers better flavor and texture in this recipe.

How Do I Prevent The Cookies From Sticking?

Grease each muffin cup generously and invert while still warm for best release.

What If I Don’t Have Maraschino Cherries?

You can skip them or use dried cherries or a small piece of strawberry instead.

Can I Make These Cookies Ahead Of Time?

Yes, they store well and can be made a day or two in advance.

Can I Bake These On A Cookie Sheet Instead?

No, they need the structure of a muffin tin to hold the topping in place.

How Can I Make Them Vegan?

Use vegan butter, a flax egg substitute, and a plant-based cookie dough.

Will These Get Soggy Overnight?

They may soften slightly but retain good texture if stored properly.

Can I Double The Recipe?

Yes, double all ingredients and use two muffin tins or bake in batches.

Conclusion

Pineapple Upside Down Sugar Cookies are a creative and delicious way to enjoy the tropical flavors of a classic dessert in convenient cookie form. With their soft, buttery base and caramelized fruit topping, these cookies are sure to be a hit at any gathering—or simply as a sweet pick-me-up for yourself. They’re easy to make, fun to eat, and packed with sunshine in every bite.

More Fun & Fruity Desserts to Try

Looking for more sweet treats with a tropical twist? Don’t miss these flavorful favorites:

Craving a creamy indulgence? The Blueberry Cream Cheese Crumb Bars are sweet, tangy, and perfect for sharing.

For a bright citrus bite, try our Key Lime Pie Bars — refreshing and rich with a graham crust crunch.
Celebrate summer any time of year with Peach Cobbler Egg Rolls — crispy, gooey, and totally crave-worthy.
Or go classic with a twist in our Strawberry Buttermilk Pound Cake — moist, fruity, and deliciously dense.

Pineapple Upside Down Sugar Cookies

Author: Chef Clara
Total Time: 35 minutes

Yield: 12 cookies 1x
Diet: Vegetarian

Print Recipe

Description

Sweet and buttery pineapple upside down sugar cookies with caramelized fruit topping—perfect for tropical dessert lovers and party treats.

Ingredients

Scale

1/2 cup unsalted butter, softened
1 cup granulated sugar
1 large egg

1 teaspoon vanilla extract
2 cups all-purpose flour
1/2 teaspoon baking powder

1/4 teaspoon salt
1/4 cup unsalted butter, melted
1/2 cup brown sugar

12 maraschino cherries
1 cup pineapple tidbits, well-drained

Cook Mode Prevent your screen from going dark

Instructions

Preheat oven to 350°F (175°C). Grease a 12-cup muffin tin.

In a small bowl, mix melted butter and brown sugar. Spoon about 1 teaspoon of the mixture into each muffin cup.
Place one maraschino cherry in the center of each cup, then add a few pineapple tidbits around the cherry.
In a large bowl, cream together softened butter and granulated sugar until light and fluffy.

Beat in the egg and vanilla extract until combined.
In a separate bowl, whisk together flour, baking powder, and salt. Gradually add the dry ingredients to the wet mixture and mix until a dough forms.
Roll dough into 12 equal balls and flatten slightly. Place each piece of dough on top of the fruit mixture in the muffin cups.

Bake for 18–22 minutes, or until the edges are golden.
Let cool in the pan for 5–10 minutes. Run a knife around the edges and carefully invert onto a wire rack or tray while still warm.
Serve warm or cooled.

Notes

Ensure pineapple is well-drained to avoid soggy bottoms.
Use silicone muffin pans for easier release.
Serve with a scoop of vanilla ice cream for an indulgent treat.

Prep Time: 15 minutes
Cook Time: 20 minutes
Category: Dessert

Method: Baking
Cuisine: American

Nutrition

Serving Size: 1 cookie

Calories: 210
Sugar: 18g
Sodium: 70mg

Fat: 10g
Saturated Fat: 6g
Unsaturated Fat: 3g

Trans Fat: 0g
Carbohydrates: 28g
Fiber: 0g

Protein: 2g
Cholesterol: 30mg