Pineapple Upside Sugar Cookies

Why You’ll Love This Recipe

• Combines the flavors of pineapple upside-down cake with soft sugar cookies
• Beautiful presentation with caramelized pineapple and cherries
• A fun and unique twist on classic sugar cookies
• Perfect balance of buttery, sweet, and tangy flavors
• Great for sharing or enjoying as a personal treat

Ingredients

(Tip: You’ll find the full list of ingredients and measurements in the recipe card below.)

For the Cookies:

• 1 cup butter, room temperature
• 1 ½ cups granulated sugar
• 2 large eggs
• 2 teaspoons vanilla extract
• ½ cup sour cream
• 3 cups all-purpose flour
• 1 teaspoon baking powder
• 1 teaspoon cornstarch
• ½ teaspoon salt

For the Toppings:

• 13 canned pineapple slices (drained)
• 13 maraschino cherries
• ½ cup melted butter
• 1 cup packed light brown sugar

Directions

Step 1: Prepare the Cookie Dough

1. In a large mixing bowl, cream together the butter and granulated sugar until light and fluffy.
2. Add the eggs one at a time, beating well after each addition. Mix in the vanilla extract and sour cream until smooth.
3. In a separate bowl, whisk together the flour, baking powder, cornstarch, and salt.
4. Gradually add the dry ingredients to the wet ingredients, mixing until a soft dough forms.
5. Cover and chill the dough in the refrigerator for at least 30 minutes.

Step 2: Prepare the Pineapple Topping

1. Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper.
2. In a small bowl, combine the melted butter and brown sugar to create a caramel-like mixture.
3. Lay out the pineapple slices on the prepared baking sheet.
4. Spoon about 1 tablespoon of the caramel mixture over each pineapple slice and place a maraschino cherry in the center.

Step 3: Shape and Bake the Cookies

1. Scoop out about 2 tablespoons of cookie dough and flatten it into a disc that matches the size of the pineapple slices.
2. Place the dough discs on top of the prepared pineapple slices, pressing gently to adhere.
3. Bake for 12-14 minutes, or until the edges of the cookies are lightly golden and the pineapple caramelizes.
4. Let the cookies cool on the baking sheet for 5 minutes before carefully flipping them over to reveal the pineapple topping.
5. Transfer to a wire rack to cool completely.

Servings and Timing

• Servings: Makes 13 cookies
• Prep Time: 40 minutes (including chilling time)
• Cook Time: 12-14 minutes
• Total Time: Approximately 55 minutes

Variations

• Coconut Twist: Add shredded coconut to the cookie dough for extra tropical flavor.
• Rum Flavoring: Add a teaspoon of rum extract to the dough for a more authentic pineapple upside-down cake taste.
• Spiced Version: Sprinkle a pinch of cinnamon or nutmeg into the brown sugar mixture for a warm spice kick.
• Mini Versions: Use pineapple tidbits instead of slices and shape smaller cookies for bite-sized treats.
• Gluten-Free: Substitute all-purpose flour with a 1:1 gluten-free baking blend.

Storage/Reheating

• Storage: Keep cookies in an airtight container at room temperature for up to 3 days. Refrigerate for up to a week.
• Freezing: Freeze cookies in a single layer, then transfer to a freezer-safe bag. Store for up to 2 months. Thaw at room temperature before serving.
• Reheating: Warm cookies in the microwave for 10-15 seconds to soften and enhance flavors.

FAQs

1. Can I use fresh pineapple instead of canned?

Yes, but make sure to slice it thinly and pat it dry to remove excess moisture.

2. Do I need to flip the cookies after baking?

Yes, flipping them reveals the caramelized pineapple topping for the signature look.

3. Can I make the dough ahead of time?

Absolutely! The dough can be refrigerated for up to 24 hours before baking.

4. Can I use a sugar substitute?

You can try using a sugar alternative like monk fruit or coconut sugar, but the texture may slightly change.

5. How do I prevent the cookies from sticking to the pan?

Lining the baking sheet with parchment paper or a silicone baking mat helps prevent sticking.

6. Can I make these cookies without eggs?

Yes! Replace eggs with unsweetened applesauce or a flax egg for an egg-free version.

7. What’s the best way to get the perfect caramelization?

Make sure the brown sugar and butter mixture is evenly distributed over the pineapple before baking.

8. Can I use homemade cookie dough?

Yes! If you have a favorite sugar cookie recipe, feel free to use it instead.

9. Why is my dough too sticky?

If your dough is too sticky, chill it longer or add a little more flour until it’s easier to handle.

10. Can I use different fruit toppings?

Yes! Try peach slices, apple rings, or even banana slices for a fun twist.

Conclusion

Pineapple Upside Sugar Cookies are the perfect fusion of a classic pineapple upside-down cake and a soft, buttery cookie. With a caramelized pineapple topping and a chewy cookie base, these treats are not only delicious but also visually stunning. Whether for a party, a special occasion, or just a tropical-inspired snack, these cookies will be a hit. Try them today and enjoy a taste of paradise in every bite!