Tropical Twist: Pineapple Upside Down Sugar Cookies Recipe

Sweet and tangy pineapple upside down sugar cookies bring a delightful twist to a classic dessert favorite.

These golden-brown treats blend nostalgic flavors with a modern bakery spin.

Traditional cake inspiration meets cookie perfection in this delectable recipe.

Each bite delivers a caramelized pineapple punch that melts in your mouth.

Buttery sugar cookie base provides the perfect foundation for the tropical fruit topping.

The combination creates an irresistible dessert that’s both familiar and surprisingly innovative.

Bake these cookies for a quick, crowd-pleasing indulgence that’s sure to spark joy at any gathering.

Quick Recipe Overview

Prep Time: 20 minutes

Cook Time: 25 minutes

Total Time: 45 minutes

Calories: 267 kcal

Servings: 13

Pineapple Upside Down Sugar Cookies Ingredient Guide

• Butter: Provides rich, creamy flavor and helps create a tender cookie texture. Choose unsalted butter for better control of salt levels.
• Granulated Sugar: Sweetens and helps create a light, crisp cookie structure. Look for fine, white crystals for smooth mixing.
• Sour Cream: Adds moisture and tanginess, ensuring a soft, tender cookie. Select full-fat sour cream for best results.

• All-Purpose Flour: Forms the structural base of the cookie. Opt for fresh, sifted flour to prevent lumps.
• Baking Powder: Creates lift and helps cookies rise evenly. Check expiration date for maximum rising power.
• Cornstarch: Enhances cookie tenderness and provides a delicate crumb. Use pure cornstarch without additives.
• Salt: Balances sweetness and enhances overall flavor. Use fine table salt for even distribution.

• Brown Sugar: Creates a rich, caramel-like base and helps with cookie's golden color. Choose dark brown sugar for deeper flavor.
• Eggs: Bind ingredients and add richness. Use fresh, room-temperature eggs for smooth mixing.
• Vanilla Extract: Adds depth and aromatic sweetness. Select pure vanilla extract for best flavor.
• Pineapple Slices: Provides tropical fruity taste and signature visual appeal. Choose canned pineapple rings for consistent size.
• Maraschino Cherries: Adds vibrant color and sweet-tart burst. Select bright red, plump cherries.

Tools to Make Pineapple Upside Down Sugar Cookies

• Mini Round Cake Pan: Essential for creating individual upside-down cookies with perfect caramelized bottoms.
• Large Mixing Bowl: Perfect for creaming butter and sugar, and mixing wet ingredients.
• Separate Mixing Bowls: Needed for combining dry ingredients and brown sugar mixture.
• 3-Tablespoon Cookie Scoop: Helps portion cookie dough evenly for consistent sizes.
• Offset Spatula: Great for smoothing and flattening cookie dough in the pan.
• Whisk: Useful for blending dry ingredients smoothly.
• Wax Paper: Helps catch any dripping caramel when turning out cookies.

Steps to Bake Pineapple Upside Down Sugar Cookies

Tropical Cookie Adventure

• Buttery Base Preparation

Blend soft butter and sugar until creamy and smooth, creating a fluffy foundation for your delightful treats.

• Wet Ingredient Fusion

Combine eggs, vanilla, and sour cream, stirring until everything melds together beautifully.

• Dry Ingredient Harmony

Whisk flour, baking powder, cornstarch, and salt in a separate bowl, then gently fold into the wet mixture until just combined.

• Caramel Candy Layer

Create a rich brown sugar and butter mixture, spreading a thin layer in the bottom of each mini cake pan.

• Tropical Fruit Placement

Arrange fresh pineapple slices and vibrant maraschino cherries atop the caramel base, setting the stage for a delicious surprise.

• Cookie Dough Topping

Scoop cookie dough generously over the fruit, smoothing it carefully to ensure even coverage.

• Baking Magic

Slide the pan into a warm 350°F oven, baking until edges turn golden and caramel bubbles around the sides, approximately 25 minutes.

• Cooling and Revealing

Let cookies rest briefly in the pan, then gently invert onto a surface, allowing any extra caramel to drizzle down.

• Serving Suggestion

Allow cookies to cool completely, then serve and enjoy these tropical-inspired treats within a few days for maximum deliciousness.

Tips for Pineapple Upside Down Sugar Cookie Perfection

• Swap pineapple with fresh peaches, apricots, or mandarin orange slices for delightful seasonal variations that transform the cookie's taste.
• Add warm spices like cinnamon, cardamom, or ginger to the cookie dough for an unexpected aromatic twist that complements the sweet caramel base.
• Separate cookie layers with parchment paper when refrigerating to prevent sticking and maintain their delicate caramelized texture for maximum freshness.
• Sprinkle toasted coconut flakes, chopped nuts, or a light dusting of powdered sugar on top to elevate the visual appeal and add delightful textural contrast.

Serving Pineapple Upside Down Sugar Cookies Fresh

• Tropical Dessert Platter: Create a vibrant display by arranging the pineapple upside down sugar cookies on a wooden board with fresh pineapple slices, toasted coconut flakes, and a small scoop of vanilla bean ice cream.
• Brunch Companion: Pair these delightful cookies with a tropical smoothie or a light rum-infused coffee for a delectable weekend brunch experience that transports you to a sunny beach paradise.
• Gifting Delight: Package these cookies in a clear gift box tied with a rustic twine, adding a small tag with a personalized message for a charming homemade present that shows thoughtfulness and culinary creativity.
• Tea Time Treat: Serve these cookies alongside a chilled glass of iced tropical tea or a warm Earl Grey, creating a perfect afternoon snack that balances sweet and tangy flavors.

How to Keep Pineapple Upside Down Sugar Cookies Good

• Quick Cooling Strategy: Let cookies rest on a wire rack to prevent soggy bottoms and maintain their delightful crisp texture.
• Refrigeration Wisdom: Store these delectable treats in an airtight container, placing a layer of parchment paper between each cookie to prevent sticking and preserve their individual charm.
• Room Temperature Magic: Keep cookies at a cool, dry spot away from direct sunlight to maintain their optimal flavor and soft-chewy consistency for up to 3 days.
• Freezing Option: Wrap individual cookies tightly in plastic wrap, then place in a freezer-safe container. These sweet treats can be frozen for up to 2 weeks, offering a delicious surprise whenever a craving strikes.

Sweet Pineapple Upside Down Sugar Cookies

---

5 Stars 4 Stars 3 Stars 2 Stars 1 Star

4.9 from 37 reviews

• Total Time: 45 minutes
• Yield: 13 1x

Print Recipe

Description

Spiced pineapple upside down sugar cookies blend tropical sweetness with classic bakery charm. Golden caramelized edges and rich buttery notes invite bakers to savor each delightful bite.

---

Ingredients

Scale 1x2x3x

• 1 cup (226 g/8 oz) butter, room temperature
• 1 ½ cups (300 g/10.5 oz) granulated sugar
• 2 eggs
• 1 cup (220 g/7.75 oz) light brown sugar, packed
• 3 cups (375 g/13.25 oz) all-purpose flour
• 13 canned pineapple slices
• 13 maraschino cherries
• ½ cup (120 g/4.25 oz) sour cream
• ½ cup (113 g/4 oz) butter, melted
• 2 tsps (10 mL) vanilla extract
• 1 tsp baking powder
• 1 tsp cornstarch
• ½ tsp salt

Cook Mode Prevent your screen from going dark

---

Instructions

1. Oven Preparation: Preheat oven to 350°F (175°C) and position mini round cake pan for the pastry.
2. Butter Mixture: Cream softened butter and granulated sugar until light and fluffy, then blend in eggs, vanilla extract, and sour cream until thoroughly combined.
3. Dry Ingredient Integration: Whisk flour, baking powder, cornstarch, and salt, then gently fold into the wet ingredients to create a smooth cookie dough.
4. Caramel Foundation: Whisk melted butter with brown sugar, then evenly distribute across the bottom of each mini cake pan cavity.
5. Fruit Placement: Arrange pineapple slices over the caramel base, positioning a maraschino cherry at the center of each slice.
6. Dough Application: Portion cookie dough over the pineapple arrangement, smoothing with an offset spatula to create a uniform surface.
7. Baking Process: Bake for 25 minutes, monitoring for golden-brown edges and bubbling caramel.
8. Cooling and Serving: Rest cookies in the pan for 10 minutes, then carefully invert onto wax paper, adjusting any displaced fruit. Allow to cool completely before serving.
9. Storage: Preserve in an airtight container, consuming within 2-3 days for optimal taste and texture.

Notes

• Caramelize with Care: Evenly spread the brown sugar mixture to create a perfect sticky base that ensures each cookie has a consistent, rich caramel flavor.
• Precise Pineapple Placement: Position pineapple slices and cherries carefully before adding cookie dough to guarantee a beautiful, professional-looking presentation.
• Cooling Technique: Let cookies rest in the pan for 10 minutes after baking to help them set and prevent breaking during the delicate inverting process.
• Storage Smart: Keep cookies in an airtight container to maintain moisture and freshness, consuming within 2-3 days for the best taste and texture.

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

Nutrition

• Serving Size: 13
• Calories: 267
• Sugar: 18 g
• Sodium: 95 mg
• Fat: 12 g
• Saturated Fat: 7 g
• Unsaturated Fat: 3 g
• Trans Fat: 0 g
• Carbohydrates: 38 g
• Fiber: 0.5 g
• Protein: 2 g
• Cholesterol: 34 mg