Sweet Flipped Pineapple Upside-Down Sugar Cookies Recipe

Sweet and nostalgic, these pineapple upside-down sugar cookies bring a delightful twist to a classic dessert.

Soft, buttery sugar cookies serve as the perfect canvas for caramelized pineapple magic.

Each bite delivers a burst of tropical flavor that dances across your taste buds.

The golden-brown edges hint at the delectable treat waiting to be savored.

Juicy pineapple rings nestled atop tender cookies create a stunning visual and flavor experience.

Bakers of all skill levels can easily master this simple yet impressive dessert.

Dive into this delectable recipe and treat yourself to a slice of tropical bliss.

Quick Recipe Overview

Prep Time: 15 minutes

Cook Time: 15 minutes

Total Time: 30 minutes

Calories: 210 kcal

Servings: 11

What You’ll Need For Pineapple Upside-Down Sugar Cookies

• Unsalted Butter: Creates a rich, caramelized base that helps the fruit stick and adds deep flavor complexity.
• Brown Sugar: Transforms into a luscious golden syrup that coats the bottom of each cookie with sweet, molasses-like richness.
• Maraschino Cherries: Adds a vibrant pop of color and classic retro dessert charm with their bright red appearance.
• Canned Pineapple Chunks: Delivers tropical sweetness and tender texture, perfectly complementing the cookie's base.

• All-Purpose Flour: Provides the essential structure and tender crumb for the classic sugar cookie foundation.
• Granulated Sugar: Sweetens the dough and helps create a delicate, crisp exterior.
• Unsalted Butter: Ensures rich, buttery flavor and helps create a soft, melt-in-your-mouth texture.
• Eggs: Bind the ingredients together and add moisture to the cookie dough.
• Vanilla Extract: Introduces a warm, aromatic depth that enhances the overall sweetness.

• Baking Powder: Helps the cookies rise and become light and fluffy.
• Salt: Balances the sweetness and amplifies the other flavors in the cookie.

Best Tools For Pineapple Upside-Down Sugar Cookies

• Muffin tin: Essential for creating individual cookie cups with caramelized topping.
• Non-stick cooking spray: Ensures easy release of cookies from the pan.
• Small bowl: Perfect for mixing melted butter and brown sugar.
• Measuring teaspoon: Helps distribute sugar mixture evenly in each muffin cup.
• Cutting board: Useful for arranging pineapple chunks and cherries.
• Knife: Needed to cut pineapple and halve cherries if necessary.

Bake Pineapple Upside-Down Sugar Cookies Like This

• Oven Preparation

Warm up the kitchen companion to a cozy 350 degrees, creating the perfect environment for baking magic. Grab your trusty muffin tin and give it a quick spray of non-stick goodness.

• Caramel Foundation

Blend the golden melted butter with rich brown sugar, creating a sweet base that will transform ordinary cookies into a tropical delight. Gently cascade a small spoonful of this liquid sunshine into each muffin cup.

• Fruity Landscape

Artfully nestle vibrant pineapple pieces and cheerful cherries into the sugary pool, crafting a delectable canvas that promises a burst of tropical flavor in every bite. Each cup becomes a miniature work of edible art, waiting to surprise and enchant taste buds with its unexpected twist on traditional cookies.

• Cookie Creation

Pour your prepared cookie dough into the decorated muffin cups, ensuring each pocket is filled with promise. The dough will cuddle around the fruit, creating a harmonious blend of textures and tastes.

• Baking Transformation

Slide the muffin tin into the warm oven, letting the heat work its magic. Watch as the cookies rise and golden brown, their edges crisping while the fruity bottom caramelizes into a glossy, irresistible treat.

• Cooling and Serving

Once baked to perfection, let the cookies rest briefly. Carefully invert the tin, allowing each cookie to reveal its stunning upside-down design – a sweet surprise that combines comfort and exotic flair.

Tweak Pineapple Upside-Down Sugar Cookies Easily

• Caramelization Trick: Let the butter and brown sugar mixture cool slightly before adding pineapple to prevent fruit from sinking and ensure a perfect golden-brown topping.
• Make-Ahead Magic: Prepare the muffin tin mixture up to 24 hours in advance and refrigerate, allowing flavors to meld and deepen before baking.
• Gluten-Free Option: Swap standard flour with a gluten-free all-purpose blend to make these cookies safe for those with wheat sensitivities while maintaining the same delicious texture.
• Dairy-Free Swap: Replace butter with coconut oil or vegan margarine to create a completely dairy-free version that still delivers rich, caramelized flavor and tender cookie texture.
• Storage Wisdom: Store cooled cookies in an airtight container at room temperature for up to 3 days, separating layers with parchment paper to prevent sticking and maintain their delicate structure.

Great Ways To Share Pineapple Upside-Down Sugar Cookies

• Tropical Dessert Plate: Serve these cookies on a vibrant platter with fresh pineapple slices and mint leaves for a stunning tropical presentation.
• Sweet Brunch Companion: Pair these cookies with a light mimosa or fresh coffee for a delightful weekend morning treat that brings sunshine to your table.
• Scoop & Serve: Top each cookie with a small scoop of vanilla bean ice cream or whipped cream to add a creamy contrast to the caramelized pineapple flavor.
• Party Platter Perfection: Arrange these mini cookies on a decorative tray with toothpicks for easy grab-and-go bites during gatherings or potluck events.

How To Keep Pineapple Upside-Down Sugar Cookies Fresh

• Cookie Batch Freshness: Store cookies in an airtight container at room temperature for up to 4 days. Layer between parchment paper to prevent sticking and maintain their delicate texture.
• Refrigeration Strategy: Keep leftover cookies in the refrigerator for extended freshness, lasting up to a week. Wrap individually in plastic wrap to preserve moisture and prevent flavor absorption.
• Freezing Technique: Freeze baked cookies flat on a baking sheet, then transfer to a freezer-safe container. These cookies can stay delicious for 2-3 months when properly sealed.
• Make-Ahead Magic: Prepare the brown sugar and butter mixture, chop pineapple chunks, and cut cherries one day before baking. Store prepared ingredients separately in the refrigerator to save time during actual cookie preparation.

Sweet Pineapple Upside-Down Sugar Cookies Recipe

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4.7 from 37 reviews

• Total Time: 30 minutes
• Yield: 11 1x

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Description

Delightful pineapple upside-down sugar cookies blend classic cake nostalgia with cookie charm. Sweet caramelized pineapple tops crisp, buttery cookies that will transport you directly to dessert paradise.

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Ingredients

Scale 1x2x3x

• 1 can pineapple rings (fresh or canned)
• ½ cup maraschino cherries
• ½ cup (113 g) unsalted butter
• ½ cup brown sugar
• 2 cups (240 g) all-purpose flour
• ¾ cup (150 g) granulated sugar
• ½ cup (113 g) unsalted butter, softened
• 1 large egg
• 1 tsp vanilla extract
• 1 tsp baking powder
• ¼ tsp salt

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Instructions

1. Muffin Tin Preparation: Lavishly coat each cavity with non-stick spray, ensuring seamless cookie extraction without sticking.
2. Caramel Foundation: Whisk melted butter and brown sugar into a silky, luminous mixture that promises decadent flavor depth for the cookies.
3. Fruit Placement: Meticulously arrange pineapple chunks and maraschino cherries in an artistic pattern, positioning each piece precisely against the muffin cup walls to create a stunning visual landscape when ultimately inverted.
4. Dough Application: Gently layer cookie dough over the fruit base, delicately distributing the mixture to preserve the intricate tropical arrangement underneath, ensuring complete coverage without disrupting the carefully curated design.
5. Baking Process: Heat oven to the specified temperature, allowing the cookies to transform, with caramel bubbling and fruit caramelizing while the dough bakes to golden perfection, creating a harmonious blend of textures and flavors.
6. Final Presentation: Once baked, immediately invert the muffin tin onto a serving platter, allowing the cookies to reveal their gorgeous pineapple-topped masterpiece, with caramelized fruit glistening against the tender cookie base.

Notes

• Prep Pan Perfectly: Generously spray muffin tin with non-stick cooking spray to guarantee seamless cookie removal without sticking or breaking.
• Master Caramel Layer: Whisk melted butter and brown sugar thoroughly until silky smooth, ensuring complete sugar dissolution for rich, even caramelization.
• Fruit Placement Strategy: Arrange pineapple chunks and cherries with precision, pressing gently against tin walls to create an attractive, professional-looking design when cookies are flipped.
• Gentle Dough Application: Carefully spoon cookie dough over fruit layer without disrupting the carefully crafted tropical arrangement, maintaining the decorative bottom design.

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

Nutrition

• Serving Size: 11
• Calories: 210
• Sugar: 15 g
• Sodium: 150 mg
• Fat: 10 g
• Saturated Fat: 6 g
• Unsaturated Fat: 4 g
• Trans Fat: 0 g
• Carbohydrates: 30 g
• Fiber: 1 g
• Protein: 2 g
• Cholesterol: 25 mg