Sunshine-Sweet Pineapple Upside-Down Sugar Cookies Recipe

Sweet memories of childhood baking come flooding back with this nostalgic pineapple upside-down sugar cookies creation.

Buttery dough carries tropical hints of caramelized fruit and warm spices.

Delicate golden edges promise a delightful crunch that melts in your mouth.

Classic comfort meets unexpected twists in this delectable treat.

Bright yellow pineapple pieces nestle into soft, tender cookie landscapes.

Vibrant colors and rich textures invite you to savor each bite.

Bake these cookies and watch smiles bloom around your kitchen.

What Makes Pineapple Upside-Down Sugar Cookies Stand Out

• Quick and Easy Tropical Treat: Whip up delightful pineapple upside-down sugar cookies that transform classic dessert into bite-sized perfection.
• Minimal Skill Required: Perfect for beginner bakers with simple ingredients and straightforward steps, guaranteeing success even for novice cookie makers.
• Family-Friendly Dessert: Create memorable moments together by preparing these colorful, sweet treats that kids and adults will absolutely adore.
• Versatile Occasion Delight: Ideal for summer gatherings, potlucks, birthday parties, or casual weekend baking adventures with minimal preparation time.

What You’ll Use in Pineapple Upside-Down Sugar Cookies

• All-Purpose Flour: Provides structure and texture for the cookie dough.
• Baking Powder, Baking Soda: Helps cookies rise and become light and fluffy.
• Salt: Enhances overall flavor of the cookie.

• Unsalted Butter: Adds richness and helps create a tender cookie texture.
• Granulated Sugar: Provides sweetness and helps with cookie browning.
• Brown Sugar: Adds deep caramel flavor and moisture to the topping.

• Egg: Binds ingredients together and adds structure to the cookie.
• Vanilla Extract: Provides warm, classic bakery flavor.
• Pineapple Slices: Offers tropical fruity taste and creates signature upside-down design.
• Maraschino Cherries: Adds bright color and sweet accent to the cookie.

Flipping Pineapple Sugar Cookies Upside-Down

Step 1: Warm Up the Oven

Set your oven to a cozy 350°F.

Line two baking sheets with parchment paper for a smooth cookie adventure.

Step 2: Whip Up the Cookie Base

• Softened butter
• Granulated sugar
• Egg
• Vanilla extract
• All-purpose flour
• Baking powder
• Baking soda
• Salt

Cream butter and sugar until they become fluffy and dreamy.

Crack in the egg and splash of vanilla, mixing until everything hugs together perfectly.

In another bowl, blend the dry ingredients.

Gently fold the dry mix into the wet ingredients, stopping just as everything comes together.

Step 3: Create the Caramel-Like Topping

Melt butter and brown sugar in a small pan over medium heat.

Stir constantly until the mixture transforms into a silky, bubbly magic sauce.

Step 4: Build Your Cookie Masterpiece

Drizzle the buttery caramel into the center of each cookie spot on the baking sheet.

Nestle a pineapple slice on top, then gently place a bright maraschino cherry right in the middle.

Carefully spread a scoop of cookie dough over each pineapple slice, letting some fruity goodness peek through.

Step 5: Bake to Golden Perfection

Slide the cookies into the oven and bake for 12-15 minutes.

Watch for those edges to turn a gorgeous golden brown.

Let the cookies rest on the baking sheet for 5 minutes, then transfer to a wire rack to cool completely.

Savor these tropical-inspired treats warm or at room temperature!

Sugar Cookie Prep Ideas for Pineapple Upside-Down Style

Position pineapple slices precisely in the center of each cookie for a picture-perfect presentation.

Let cookies rest on the baking sheet for exactly 5 minutes before transferring to prevent breaking delicate edges.

Cream butter and sugar thoroughly until light and fluffy to ensure a soft, tender cookie texture.

Choose bright, vibrant maraschino cherries for a pop of color and sweet, tangy flavor in each bite.

Avoid overmixing cookie dough to prevent tough, dense cookies – mix just until ingredients are combined.

Store Pineapple Upside-Down Sugar Cookies

• Store cookies in an airtight container for up to 3 days, separating layers with parchment paper to prevent sticking.
• Wrap individual cookies tightly in plastic wrap, then place in a freezer bag for up to 2 months; thaw at room temperature for best texture.
• Warm cookies briefly in a preheated 300°F oven for 3-5 minutes to restore their soft, fresh-baked texture and revive the caramelized topping.
• Enjoy reheated cookies with a scoop of vanilla ice cream or a dollop of whipped cream for an extra special treat.

Ideas to Serve with Pineapple Sugar Cookies

• Savor Sweet Rum Cocktail: Blend a tropical-inspired rum punch with pineapple juice, coconut cream, and a splash of grenadine to complement the cookie's fruity flavors.
• Pair with Coconut Vanilla Latte: Create a creamy, smooth coffee drink using coconut milk and a hint of vanilla extract that echoes the cookie's caramelized sweetness.
• Match with Tropical Fruit Sorbet: Serve a light, refreshing pineapple or mango sorbet alongside the cookies to enhance the tropical fruit notes and provide a cool contrast.
• Complement with Salted Caramel Ice Cream: Scoop rich, buttery salted caramel ice cream that harmonizes with the cookie's brown sugar topping and adds delightful depth.

Upside-Down Cookies Fruit Choices

• Gluten-Free Pineapple Paradise: Swap all-purpose flour with a gluten-free blend, ensuring same texture and taste for those with wheat sensitivities.
• Vegan Tropical Treat: Replace butter with coconut oil, use a flax egg instead of regular egg, and select plant-based maraschino cherries to create a completely dairy-free and animal-product-free version.
• Low-Sugar Fruity Cookie: Substitute brown sugar with monk fruit sweetener, use fresh pineapple chunks instead of canned, and reduce overall sugar content for a healthier alternative that maintains delicious flavor.
• Nutty Tropical Crunch: Sprinkle chopped macadamia nuts or toasted coconut flakes over the cookie before baking, adding extra crunch and complementing the pineapple's tropical profile.

FAQs

• How do I ensure the pineapple stays moist and doesn't dry out during baking?

The key is to use fresh or well-drained canned pineapple slices and not to overbake the cookies. The butter-sugar mixture helps keep the fruit tender, and watching the baking time carefully prevents drying.

• Can I make these cookies ahead of time?

Yes, you can prepare the cookie dough and topping mixture in advance. Store the dough in the refrigerator for up to 2 days, and prepare the topping just before baking. This makes it easy to have fresh cookies ready quickly.

• What's the best way to remove the cookies from the baking sheet?

After letting the cookies cool for 5 minutes, use a thin spatula to gently lift them off the parchment paper. The caramelized sugar might make them slightly sticky, so take care when transferring.

• How can I tell if the cookies are perfectly baked?

Look for light golden brown edges and a set center. The cookies should look slightly soft when you remove them from the oven, as they’ll continue to firm up while cooling on the baking sheet.

Pineapple Upside-Down Sugar Cookies Recipe

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4.7 from 35 reviews

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

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Description

Pineapple upside-down sugar cookies deliver a delightful twist on classic dessert nostalgia. Sweet caramelized fruit nestles atop buttery sugar cookies, creating a charming treat reminiscent of traditional cake that will delight your senses.

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Ingredients

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Main Ingredients (Cookies):

• 2 1/2 cups all-purpose flour
• 1 cup unsalted butter, softened
• 1 cup granulated sugar
• 1 large egg

Fat and Leavening Agents:

• 1 teaspoon baking powder
• 1/2 teaspoon baking soda
• 1/2 teaspoon salt
• 1 teaspoon vanilla extract

Topping Ingredients:

• 1 can (8 ounces/226 grams) pineapple slices, drained (reserve juice)
• 1/4 cup unsalted butter
• 1/2 cup brown sugar, packed
• Maraschino cherries (one for each cookie)

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Instructions

1. Prepare the caramel base by melting butter and brown sugar in a saucepan over medium heat, stirring until the mixture transforms into a smooth, glossy liquid.
2. Carefully distribute the caramel mixture across the prepared baking sheets, creating a thin, even layer in each designated cookie spot.
3. Arrange pineapple slices strategically on top of the caramel, ensuring each slice sits centered and flat.
4. Position a vibrant maraschino cherry in the middle of each pineapple slice, creating a classic upside-down cake aesthetic.
5. Cream softened butter with granulated sugar until the mixture becomes light and airy, developing a fluffy texture that will contribute to the cookie’s delicate structure.
6. Incorporate egg and vanilla extract into the butter mixture, blending thoroughly to create a uniform consistency.
7. Whisk together flour, baking powder, baking soda, and salt in a separate bowl, ensuring even distribution of leavening agents.
8. Gently fold the dry ingredients into the wet mixture, mixing minimally to prevent overworking the dough and maintain a tender crumb.
9. Delicately spoon cookie dough over each pineapple slice, covering the fruit partially while allowing some decorative elements to peek through.
10. Transfer the cookie-laden baking sheets into a preheated 350°F oven and bake for 12-15 minutes, watching for edges to turn a delicate golden brown.
11. Remove from the oven and allow cookies to rest on the baking sheet for 5 minutes, enabling the caramel to set slightly.
12. Carefully transfer cookies to a wire rack, letting them cool completely to ensure the caramel topping stabilizes and the cookies achieve optimal texture.

Notes

• Check butter temperature before creaming to ensure smooth, even texture.
• Use room-temperature ingredients for better cookie consistency and blending.
• Avoid overmixing cookie dough to prevent tough, dense cookies.
• Drain pineapple slices thoroughly to prevent excess moisture affecting cookie texture.
• Rotate baking sheet halfway through cooking for even browning.
• Experiment with alternative fruits like peaches or cherries for unique variations.
• Store cookies in an airtight container to maintain freshness for 3-4 days.
• For gluten-free option, substitute all-purpose flour with almond or gluten-free blend.

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

Nutrition

• Serving Size: 24
• Calories: 170
• Sugar: 12 g
• Sodium: 150 mg
• Fat: 7 g
• Saturated Fat: 4 g
• Unsaturated Fat: 2 g
• Trans Fat: 0 g
• Carbohydrates: 24 g
• Fiber: 0 g
• Protein: 1 g
• Cholesterol: 20 mg