Irresistible Pineapple Upside-Down Sugar Cookies Recipe

Sweet aromas of caramelized pineapple dance through these delightful sugar cookies that promise a nostalgic twist on a classic dessert.

Memories of childhood summers blend seamlessly with buttery cookie textures.

Bright yellow fruit chunks nestle into soft, golden dough creating unexpected bursts of tropical flavor.

Soft hints of brown sugar complement the tangy pineapple perfectly.

Each bite offers a playful surprise that connects comfort and creativity.

Baking these treats will transport you to sunlit kitchen memories with loved ones.

Whip up this simple recipe and let deliciousness unfold.

Why Pineapple Upside-Down Sugar Cookies Are So Sweet

• Craft Delightful Dessert: Transform classic sugar cookies into a stunning upside-down treat that looks professionally baked with minimal effort.
• Quick Kitchen Adventure: Prepare a show-stopping dessert in just a few simple steps, perfect for bakers of all skill levels who want to impress family and friends.
• Nostalgic Flavor Twist: Combine the beloved pineapple upside-down cake concept with the simplicity of sugar cookies, creating a unique and memorable sweet experience that brings comfort and excitement to the table.
• Versatile Crowd-Pleaser: Ideal for potlucks, family gatherings, or spontaneous dessert cravings, these individual cookies offer a portable and charming alternative to traditional cake.

Ingredients for Pineapple Upside-Down Sugar Cookies

• Pineapple: Fresh fruit that provides a sweet and tangy flavor to the cookie base.
• Maraschino Cherries: Bright red cherries that add a pop of color and classic flavor to the dessert.

• Butter: Creates a rich and tender texture in the sugar cookie dough.
• Granulated Sugar: Provides sweetness and helps create a light, fluffy cookie.
• Egg: Binds the ingredients together and adds moisture to the dough.
• Vanilla Extract: Enhances the overall flavor of the sugar cookie.

• All-Purpose Flour, Baking Powder, Salt: These ingredients work together to create the perfect sugar cookie texture and help the cookies rise evenly.

• Brown Sugar, Melted Butter: Combines to create a caramelized base that gives the cookies their signature upside-down cake-like bottom.

How to Bake Pineapple Upside-Down Sugar Cookies

Step 1: Prepare the Topping

Fire up your oven to 350F (175C). Grab a muffin tin and give it a light spray or line with parchment rounds. In a small bowl, blend melted butter and brown sugar until they become best friends. Scoop about a tablespoon of this sweet mixture into each muffin cup. Lovingly place tiny pineapple pieces over the sugar mixture. Nestle a maraschino cherry right in the center of each cup, creating a vibrant design.

Step 2: Mix the Cookie Dough

• All-purpose flour
• Baking powder
• Salt

Slowly introduce the dry ingredients to the wet mixture, stirring until a soft, pillowy dough forms.

Step 3: Layer the Cookies

Scoop about 1 1/2 tablespoons of cookie dough into each muffin cup. Gently press the dough over the pineapple and cherry, making sure it covers the topping evenly like a cozy blanket.

Step 4: Bake to Golden Perfection

Slide the muffin tin into the oven and bake for 12-15 minutes. Watch for those edges to turn a beautiful golden color. Once done, let the cookies rest in the tin for 5 minutes. Then, carefully flip the tin onto a parchment-lined surface or cooling rack, revealing the gorgeous upside-down treasures.

Step 5: Serve and Enjoy

Serve these cookies warm or at room temperature. Each bite promises a burst of caramelized pineapple goodness nestled on a soft sugar cookie base. Get ready for a taste adventure that’ll make everyone smile!

Pro Tips for Pineapple Upside-Down Sugar Cookies

• Swap fresh pineapple for canned if needed, ensuring you drain excess syrup completely to prevent soggy cookies. Experiment with different fruit variations like peaches or cherries for unique flavor twists that complement the sweet sugar cookie base.
• Check cookie doneness by looking for light golden edges and a slightly firm center. Remove from oven promptly to maintain a soft, tender texture that melts in your mouth.
• Use room temperature ingredients, especially butter and egg, to create a smoother, more consistent cookie dough that blends effortlessly. Cold ingredients can result in lumpy, uneven mixtures.
• For a gluten-free version, replace all-purpose flour with a cup-for-cup gluten-free flour blend. Add an extra tablespoon of liquid if the dough seems too dry after substitution.

Variations to Try on Pineapple Upside-Down Sugar Cookies

• Tropical Paradise Cookies: Replace pineapple with mango chunks and add a sprinkle of toasted coconut flakes for a vibrant island-inspired treat.
• Spiced Autumn Version: Swap pineapple for caramelized apples and mix cinnamon and nutmeg into the cookie dough for a cozy fall flavor profile.
• Berry Blush Cookies: Use raspberry preserves and fresh strawberry slices instead of pineapple, creating a sweet and tangy fruity alternative.
• Caramel Pecan Remix: Top with chopped pecans and drizzle caramel sauce over the cookies after baking for a rich, nutty transformation.

Pairing Ideas for Pineapple Upside-Down Sugar Cookies

• Pair with Tropical Rum Cocktail: Mix light rum, pineapple juice, and a splash of coconut cream for a refreshing drink that echoes the cookie's fruity flavor profile.
• Create Vanilla Ice Cream Companion: Serve a scoop of creamy vanilla ice cream alongside the warm cookies to complement the caramelized pineapple and provide a cool contrast.
• Match with Coconut Chai Latte: Brew a spiced chai tea with steamed milk and a hint of coconut syrup to enhance the sweet and tropical notes of the upside-down cookies.
• Offer Caramel Macchiato Alongside: Prepare a rich caramel macchiato with espresso and caramel drizzle to mirror the cookie's buttery, caramelized undertones and add depth to the dessert experience.

Storage Advice for Pineapple Upside-Down Sugar Cookies

• Seal cooled cookies in an airtight container, layer with parchment paper between each cookie to prevent sticking. Keep refrigerated for up to 5 days, maintaining their soft texture and flavor.
• Wrap individual cookies tightly in plastic wrap, then place in a freezer-safe container or zip-lock bag. Freeze for maximum 2 months. Thaw at room temperature for best taste and texture.
• Place cookie on a microwave-safe plate, heat for 10-15 seconds. Check temperature to avoid overcooking. Enjoy warm, soft cookie with caramelized pineapple topping restored.
• Preheat oven to 300F, arrange cookies on baking sheet lined with parchment paper.

Frequently Asked Questions About Pineapple Upside-Down Sugar Cookies

• Can I use fresh pineapple instead of canned?

Yes, you can use fresh pineapple. Just cut it into small pieces and make sure they’re not too thick so they cook evenly with the cookie.

• Do I need any special equipment to make these cookies?

A muffin tin is essential. Parchment rounds help with easy removal, but you can also use baking spray to grease the tin.

• How do I know when the cookies are perfectly baked?

Look for lightly golden edges and a set cookie top. The cookies should look slightly firm but not dark brown. Around 12-15 minutes is typically perfect.

Pineapple Upside-Down Sugar Cookies Recipe

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4.7 from 13 reviews

• Total Time: 27-30 minutes
• Yield: 24 1x

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Description

Sweet Southern charm meets classic dessert in this Pineapple Upside-Down Sugar Cookies masterpiece. Caramelized pineapple nestled atop buttery sugar cookies brings nostalgic comfort with each delightful bite you’ll savor.

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Ingredients

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Main Ingredients:

• 1 cup unsalted butter, softened
• 1 cup granulated sugar
• 2 1/2 cups all-purpose flour
• 1 large egg
• 1 can (20 ounces/567 grams) pineapple slices, drained and cut into small pieces

Topping Ingredients:

• 1/2 cup unsalted butter, melted
• 1/2 cup brown sugar, packed
• Maraschino cherries, halved

Seasoning and Flavoring Ingredients:

• 1 teaspoon vanilla extract
• 1 teaspoon baking powder
• 1/4 teaspoon salt

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Instructions

1. Prepare the muffin tin by setting the oven to 350F (175C). Coat the tin with light grease or place parchment rounds inside each cavity.
2. Create the caramel base by whisking melted butter and brown sugar until smooth. Distribute approximately one tablespoon of this mixture into each muffin cup.
3. Strategically arrange pineapple pieces over the brown sugar mixture, then nestle a maraschino cherry half at the center of each cup.
4. In a spacious mixing bowl, whip softened butter and granulated sugar until the mixture becomes airy and pale.
5. Incorporate egg and vanilla extract, blending thoroughly until the ingredients are fully integrated.
6. Separately combine flour, baking powder, and salt through a gentle whisking motion.
7. Gradually fold the dry ingredients into the butter mixture, working until a tender dough emerges.
8. Portion roughly 1½ tablespoons of cookie dough into each muffin cup, carefully pressing the dough to cover the pineapple and cherry topping completely.
9. Transfer the muffin tin to the preheated oven and bake for 12-15 minutes, watching for golden-brown edges.
10. Allow cookies to rest in the tin for 5 minutes after removing from the oven.
11. Invert the muffin tin onto a parchment-lined surface or cooling rack to release the cookies.
12. Serve these delectable treats warm or at room temperature, showcasing the luscious caramelized pineapple topping.

Notes

• Swap butter with coconut oil for a dairy-free version that maintains rich flavor and tender texture.
• Use gluten-free flour blend to make these cookies suitable for those with wheat sensitivities, ensuring the same delightful crumbly consistency.
• Drain pineapple pieces thoroughly to prevent excess moisture from affecting cookie structure and preventing soggy bottoms.
• Experiment with alternative fruits like peaches or mandarin oranges for unique flavor variations that still complement the sweet sugar cookie base.

• Prep Time: 15 minutes
• Cook Time: 12-15 minutes
• Category: Desserts, Snacks
• Method: Baking
• Cuisine: American

Nutrition

• Serving Size: 24
• Calories: 190 kcal
• Sugar: 12 g
• Sodium: 90 mg
• Fat: 9 g
• Saturated Fat: 5 g
• Unsaturated Fat: 4 g
• Trans Fat: 0.1 g
• Carbohydrates: 26 g
• Fiber: 1 g
• Protein: 2 g
• Cholesterol: 25 mg