Quick & Sweet Pineapple Upside Down Sugar Cookies Recipe

Pineapple upside down sugar cookies bring a nostalgic twist to classic dessert traditions.

Sweet memories dance across taste buds with each delectable bite.

Caramelized fruit enhances ordinary cookies into extraordinary culinary experiences.

Golden-brown edges hint at the delightful combination waiting inside.

Soft, buttery textures meld perfectly with tangy tropical notes.

Home bakers can easily elevate their cookie game with this innovative recipe.

Unexpected flavor profiles promise to surprise and delight dessert enthusiasts.

The Charm of Pineapple Upside Down Sugar Cookies

• Reinvent Classic Dessert: Transform the traditional pineapple upside-down cake into adorable, bite-sized sugar cookies that capture all the nostalgic flavors in a cute, portable format.
• Caramelized Tropical Delight: Experience the magical combination of gooey brown sugar caramel, sweet pineapple, and vibrant maraschino cherries that create a luxurious, sticky-sweet topping with stunning visual appeal.
• Foolproof Baking Method: Enjoy an easy, beginner-friendly recipe that requires minimal technical skills, uses simple ingredients, and delivers impressive results that look like they came from a professional bakery.

Ingredients for Pineapple Upside Down Sugar Cookies

• All-Purpose Flour: Provides structure and texture for the cookie base with a fine, smooth consistency.
• Baking Powder: Helps the cookies rise and creates a light, tender crumb.
• Cornstarch: Adds softness and prevents the cookies from becoming too dense.
• Salt: Enhances overall flavor and balances the sweetness.

• Butter, Granulated Sugar: Creates a rich, creamy base with a classic sweet flavor.
• Eggs: Bind ingredients together and add moisture to the cookie dough.
• Vanilla Extract: Provides warm, aromatic depth to the cookie flavor.
• Sour Cream: Adds moisture and creates a tender, soft cookie texture.

• Brown Sugar, Melted Butter: Forms a caramel-like glaze that creates a rich, sticky bottom layer.
• Pineapple Slices: Offers a sweet, tangy tropical fruit element to the cookie.
• Maraschino Cherries: Adds a bright pop of color and sweet, fruity accent to the top of each cookie.

How to Prepare Pineapple Sugar Cookies

Step 1: Prepare the Oven

Warm up your oven to 350°F. Ready a mini round cake pan or similar baking dish.

Step 2: Create the Cookie Base

• Butter
• Granulated sugar

Continue until the mixture becomes light and fluffy.

Step 3: Blend Wet Ingredients

• Eggs
• Vanilla extract
• Sour cream

Mix thoroughly until everything combines smoothly.

Step 4: Prepare Dry Ingredients

• Flour
• Baking powder
• Cornstarch
• Salt

Whisk these ingredients together.

Step 5: Combine Wet and Dry Mixtures

Gradually fold the dry ingredients into the wet mixture. Mix until the cookie dough just comes together. Set aside.

Step 6: Craft the Caramel Base

• Melted butter
• Brown sugar

Stir until fully combined and smooth.

Step 7: Build the Cookie Foundation

Spread a tablespoon of brown sugar mixture into the bottom of each mini cake pan cavity.

Step 8: Add Fruity Layers

Place a pineapple slice on top of the brown sugar mixture.

Position a maraschino cherry in the center of each pineapple slice.

Step 9: Top with Cookie Dough

Use a 3-tablespoon cookie scoop to portion dough onto each pineapple slice.

Flatten the dough evenly using an offset spatula.

Step 10: Bake to Perfection

Slide the pan into the preheated oven.

• Cookie edges turn golden brown
• Brown sugar mixture bubbles around the sides

Step 11: Cool and Reveal

Let cookies rest in the pan for 10 minutes.

Carefully turn out onto wax paper-covered surface.

Gently reposition any stuck pineapple slices.

Step 12: Serve and Enjoy

Allow cookies to cool completely.

Store in an airtight container.

Best enjoyed within 2-3 days for optimal flavor and texture.

Tips for Baking Upside Down Cookies Right

• Prep Like a Pro: Use room temperature butter and eggs for smoother, more evenly mixed cookie dough that ensures perfect texture.
• Prevent Sticking: Lightly grease mini cake pans with cooking spray before adding brown sugar mixture to guarantee easy cookie removal.
• Fruit Placement Perfection: Gently pat pineapple slices and cherries dry with paper towels to prevent excess moisture from affecting cookie consistency.
• Even Baking Trick: Rotate the pan halfway through baking to ensure uniform golden-brown edges and consistent cookie doneness.
• Storage Savvy: Keep cookies in a single layer to maintain their delicate caramelized topping and prevent sticking or losing their beautiful shape.

Keeping and Rewarming Pineapple Cookies

• Refrigeration: Store cooled cookies in an airtight container, separating layers with parchment paper to prevent sticking. Refrigerate for up to 4 days to maintain freshness and prevent spoilage.
• Room Temperature: Keep cookies at room temperature in a sealed container for 2-3 days. Ensure the container is placed in a cool, dry spot away from direct sunlight to preserve their texture.
• Reheating: Warm cookies gently in the microwave for 10-15 seconds or in a preheated oven at 300°F for 3-5 minutes. This method helps restore their soft, delightful texture and brings back the warm, caramelized flavor of the pineapple and brown sugar.

Pairing Options for Pineapple Sugar Cookies

• Pair with Tropical Rum Cocktail: Blend a refreshing Mai Tai or Piña Colada that echoes the pineapple's sweet tropical notes, creating a vibrant flavor connection between the cookie and drink.
• Complement with Vanilla Bean Ice Cream: Serve a scoop of creamy vanilla bean ice cream alongside the warm cookie, letting the cool, smooth texture contrast beautifully with the caramelized pineapple.
• Match with Coconut Cream Coffee: Brew a rich coffee and add a splash of coconut cream, mirroring the tropical undertones of the pineapple upside down sugar cookie for a harmonious dessert experience.
• Enhance with Caramel Macchiato: The deep caramel and espresso flavors in a macchiato will beautifully highlight the brown sugar and caramelized pineapple elements in the cookie.

Creative Directions for Pineapple Upside Down Cookies

• Tropical Paradise Cookies: Swap pineapple slices with mango or passion fruit for a Caribbean-inspired treat that brings exotic flavors to your classic cookie.
• Caramel Pecan Upgrade: Replace pineapple with caramelized pecans and a drizzle of salted caramel sauce, creating a rich and nutty version of the original recipe.
• Berry Bliss Cookies: Use sliced strawberries or raspberries instead of pineapple, then sprinkle with a light dusting of powdered sugar for a fruity summer dessert.
• Coconut Cream Dream: Add shredded coconut to the cookie dough and top with toasted coconut flakes for a tropical and textural enhancement to the classic recipe.

Pineapple Upside Down Sugar Cookies Recipe

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4.8 from 26 reviews

• Total Time: 45 minutes
• Yield: 12 1x

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Description

Pineapple upside down sugar cookies blend nostalgic cake flavors with classic cookie charm. Caramelized pineapple and maraschino cherries crown buttery sugar cookie bases, offering sweet paradise in one delightful bite.

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Ingredients

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Pineapple Upside Down Sugar Cookies

Main Ingredients:

• 1 cup (226 grams) butter, room temperature
• 1 ½ cups (300 grams) granulated sugar
• 2 eggs
• 3 cups (375 grams) all-purpose flour
• 13 canned pineapple slices
• 13 maraschino cherries

Wet Ingredients:

• 2 teaspoons (10 milliliters) vanilla extract
• ½ cup (120 grams) sour cream
• ½ cup (113 grams) butter, melted
• 1 cup (220 grams) light brown sugar, packed

Dry Ingredients:

• 1 teaspoon baking powder
• 1 teaspoon cornstarch
• ½ teaspoon salt

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Instructions

1. Prepare the oven by heating to 350°F (175°C) and ready a mini round cake pan for the upcoming pastry creation.
2. Combine softened butter and granulated sugar in a large mixing bowl, whipping until the mixture becomes airy and pale.
3. Incorporate eggs, vanilla extract, and sour cream into the butter mixture, blending thoroughly until smooth.
4. In a separate container, thoroughly combine flour, baking powder, cornstarch, and salt using a whisk.
5. Gradually fold the dry ingredients into the wet ingredients, mixing gently until the cookie dough forms a cohesive texture.
6. Create a rich caramelized base by whisking melted butter with brown sugar until fully integrated.
7. Distribute a layer of the brown sugar mixture across the bottom of each mini cake pan cavity, ensuring even coverage.
8. Delicately position a pineapple slice atop the caramel base, then nestle a maraschino cherry at the center of each slice.
9. Scoop cookie dough using a portioning tool, placing dollops directly over the pineapple arrangement.
10. Smooth the dough evenly using an offset spatula, creating a uniform surface.
11. Transfer the pan to the preheated oven and bake for approximately 25 minutes, watching for golden-brown edges and bubbling caramel.
12. After removing from the oven, allow the cookies to rest in the pan for 10 minutes to stabilize.
13. Carefully invert the pan onto a wax paper-covered surface, gently repositioning any displaced pineapple slices.
14. Permit the cookies to cool completely before serving, ensuring optimal texture and flavor.
15. Store the cookies in an airtight container and consume within 2-3 days for maximum enjoyment.

Notes

• Prep Carefully: Always have ingredients at room temperature for smoother mixing and better cookie texture.
• Baking Tip: Use mini round cake pans for perfect individual servings that showcase the classic pineapple upside-down design.
• Sugar Syrup Secret: Spreading brown sugar and butter mixture evenly creates a caramelized bottom that transforms these cookies into mini dessert masterpieces.
• Cherry Placement: Position maraschino cherries precisely in the pineapple center for a traditional, visually appealing presentation.
• Cooling Critical: Let cookies rest in the pan for 10 minutes before inverting to ensure the caramel sets and prevents structural collapse.
• Storage Wisdom: These cookies maintain optimal taste and texture when consumed within 2-3 days, stored in an airtight container at room temperature.

• Prep Time: 20 minutes
• Cook Time: 25 minutes
• Category: Desserts, Snacks
• Method: Baking
• Cuisine: American

Nutrition

• Serving Size: 12
• Calories: 312
• Sugar: 26 g
• Sodium: 220 mg
• Fat: 15 g
• Saturated Fat: 9 g
• Unsaturated Fat: 4 g
• Trans Fat: 0 g
• Carbohydrates: 42 g
• Fiber: 1 g
• Protein: 2 g
• Cholesterol: 38 mg