Fun Tangy Pineapple Upside-Down Sugar Cookies Recipe for All
Sweet, buttery cookies with a nostalgic pineapple upside-down sugar cookies twist deliver a delightful dessert experience that sparks childhood memories.
Caramelized pineapple rings nestled atop soft, golden cookie bases create a stunning visual treat for any gathering.
Classic baking techniques blend seamlessly with tropical flavors in this simple yet elegant dessert.
Each bite promises a perfect balance of crisp edges and tender centers, complemented by sweet, tangy pineapple.
Warm from the oven, these cookies offer a comforting embrace of familiar yet exciting flavors.
Bakers of all skill levels can master this crowd-pleasing recipe with ease.
Prepare to delight everyone’s taste buds with these irresistible, sunshine-inspired treats.
Toppings and Twists for Pineapple Upside-Down Cookies
Caramelization Magic: Let the brown sugar and butter mixture caramelize slightly before adding pineapple for a deeper, richer flavor that enhances the overall sweetness.
Make-Ahead Trick: Prepare the cookie dough and refrigerate it overnight to allow flavors to develop and make the dough easier to handle.
Gluten-Free Swap: Replace all-purpose flour with a gluten-free flour blend to make these cookies suitable for those with gluten sensitivities.
Tropical Twist: Experiment with different fruits like mango or peach chunks instead of pineapple for a unique flavor profile that keeps the recipe exciting.
Vegan Version: Use coconut oil instead of butter and substitute eggs with a plant-based egg replacer to create a completely dairy-free and vegan-friendly cookie.
Serving Pineapple Cookies That Look as Good as They Taste
Tropical Dessert Plate Companion: Serve these delightful cookies alongside a scoop of vanilla bean ice cream for a creamy, cool contrast to the warm, caramelized fruit topping.
Brunch Crowd-Pleaser: Arrange the cookies on a beautiful platter with fresh mint leaves and additional maraschino cherries for a stunning presentation that will impress breakfast guests.
Coffee Pairing Delight: These sweet treats perfectly complement a rich espresso or cappuccino, making them an ideal mid-morning or afternoon snack that elevates your coffee break.
Picnic Perfect Treat: Pack these portable cookies in a cute container for outdoor gatherings, beach trips, or summer potlucks where their compact size and delicious flavor will be a hit with friends and family.
How to Store Pineapple Sugar Cookies with No Mess
Quick Refrigeration: Store these delightful cookies in an airtight container inside the refrigerator for up to 5 days. Keep them separated by parchment paper to prevent sticking and maintain their beautiful caramelized topping.
Freezing Friendly: Wrap individual cookies tightly in plastic wrap, then place in a freezer-safe container. These treats can be frozen for 2-3 months without losing their delicious flavor or texture. Thaw at room temperature for about 30 minutes before enjoying.
Make-Ahead Magic: Prepare the cookie dough and brown sugar-butter mixture up to 2 days in advance. Store the prepared components separately in the refrigerator, assembling and baking just before serving for maximum freshness and flavor.
Room Temperature Tips: If serving within 24 hours, keep cookies on a covered plate at room temperature. Avoid direct sunlight or heat sources to maintain their perfect caramelized edges and soft, chewy texture.
Quick Recipe Overview
Prep Time: 15 minutes
Cook Time: 15 minutes
Total Time: 30 minutes
Calories: 150 kcal
Servings: 12
Pineapple Upside-Down Sugar Cookies Ingredient List
For Topping:
Unsalted Butter: Creates a luscious caramel-like base that helps the fruit stick and adds rich flavor.
Brown Sugar: Adds deep sweetness and helps form a gooey, golden coating for the cookies.
Maraschino Cherries: Brings a burst of vibrant color and classic retro dessert charm.
Canned Pineapple Chunks: Provides juicy tropical sweetness and tender texture to each bite.
For Cookie Base:
All-Purpose Flour: Provides the essential structure and tender crumb for the cookie.
Granulated Sugar: Delivers consistent sweetness and helps create a light texture.
Baking Powder: Ensures the cookies rise and become soft and fluffy.
Salt: Balances the sweetness and enhances overall flavor profile.
Vanilla Extract: Adds warm, comforting depth and aromatic complexity.
For Wet Ingredients:
Eggs: Bind the ingredients together and contribute to the cookie's rich texture.
Vegetable Oil: Keeps the cookies moist and tender, preventing dryness.
Milk: Helps create a smooth, cohesive batter and adds subtle richness.
Tools to Flip Pineapple Upside-Down Sugar Cookies Perfectly
Muffin tin: Crucial for creating individual cookie cups with caramelized fruit bottoms.
Non-stick cooking spray: Ensures easy removal of cookies from the tin.
Small bowl: Perfect for mixing butter and brown sugar mixture.
Measuring teaspoon: Helps evenly distribute the caramel base.
Spoon: Useful for placing pineapple chunks and cherries in each cup.
Mixing bowl: Needed for preparing cookie dough (implied in later steps).
Measuring cups and spoons: Essential for accurate ingredient measurements.
How to Make Pineapple Upside-Down Sugar Cookies from Scratch
Warm Up the Oven Prepare your kitchen by heating the oven to a cozy 350°F and lightly coating a muffin tin with non-stick spray.
Create a Sweet Base Whip together melted butter and brown sugar, creating a delightful caramel-like mixture that will bring magic to the bottom of each cookie cup.
Design Your Fruity Canvas Gently place pineapple chunks and cherries into the muffin cups, arranging them with care to create a stunning edible artwork.
Mix the Cookie Dough Combine flour, baking powder, and salt in one bowl. In another, cream together butter and sugar until light and fluffy. Blend in eggs and vanilla, then slowly incorporate the dry ingredients to form a smooth, irresistible dough.
Fill the Cups Spoon the cookie dough over the fruit, carefully covering the colorful bottom layer. Make sure each cup is about two-thirds full to allow room for rising.
Bake to Perfection Slide the muffin tin into the preheated oven and bake for 18-22 minutes. Look for golden edges and a springy top that signals these treats are ready.
Flip and Reveal Let the cookies cool for just a few minutes, then carefully invert the tin onto a serving plate. Watch as the gorgeous fruity bottom becomes a stunning top, revealing a mouthwatering masterpiece.
Sweet pineapple upside-down sugar cookies offer a delightful twist on classic desserts. Rich caramelized fruit and buttery cookie base create a nostalgic treat you’ll savor with each delectable bite.
Ingredients
Scale
1 can or 6–8 fresh pineapple rings
½ cup (113 g) unsalted butter
½ cup (100 g) brown sugar
½ cup (113 g) unsalted butter, softened
½ cup (100 g) granulated sugar
1 ½ cups (180 g) all-purpose flour
1 large egg
1 tsp (5 g) baking powder
1 tsp vanilla extract
¼ tsp salt
4–6 maraschino cherries
Instructions
Preheat Preparation: Heat the oven to 350F (175C) and liberally coat a muffin tin with non-stick spray, ensuring comprehensive coverage to prevent adherence.
Caramel Foundation: Whisk melted butter and brown sugar into a silky, uniform mixture that will create a luscious base for the cookies, distributing the mixture evenly across each muffin cavity with approximately one teaspoon per cup.
Fruit Arrangement: Meticulously position pineapple chunks and halved cherries at the base of each cavity, creating an aesthetically pleasing pattern that guarantees complete fruit coverage and visual appeal.
Caramelization Process: Place the prepared tin in the preheated oven, allowing the sugary mixture to transform and the fruit to develop rich, golden caramelized edges while becoming translucent and glossy.
Cooling and Unmolding: After removing from the oven, let the cookies rest briefly to set the caramelized fruit, then carefully invert the tin onto a serving platter, gently tapping to release the cookies and showcase the beautifully glazed fruit topping.
Final Presentation: Allow the upside-down cookies to cool completely, ensuring the caramel and fruit remain perfectly bonded to the cookie base, creating a delectable and visually stunning dessert.
Notes
Prevent Sticking Carefully: Liberally coat muffin tin with non-stick spray, ensuring every surface is covered to guarantee easy cookie removal.
Caramelize Precisely: Watch sugar-butter mixture closely during baking to achieve perfect golden-brown color without burning or becoming bitter.
Fruit Placement Strategy: Arrange pineapple chunks and cherries symmetrically and gently to create visually appealing and evenly distributed fruit patterns.
Cooling Technique: Let cookies rest briefly after baking before inverting, allowing caramel to set and minimize potential structural breakdown during serving.
Recipe development with a focus on single-dish meals.
Fusion of traditional and modern Australian cuisines.
Food styling and photography for digital platforms.
Education
Box Hill Institute, Melbourne
Degree: Advanced Diploma of Hospitality Management
Focus: Specialized in practical food and beverage service, responsible alcohol and hygiene compliance, legal risk management, and hands‑on experience in a simulated restaurant environment.
William Angliss Institute, Melbourne
Program: Certificate IV in Patisserie
Focus: Specialized in pastry and bakery techniques, cookery and specialty food preparation, recipe planning and costing, commercial kitchen operations, sustainable and inclusive work practices, food safety and hygiene compliance, and workplace health and safety.
Jenna is the heart of Picture Perfect Meals, turning simple ingredients into beautiful, easy‑to‑make dishes.
Growing up around family meals in Melbourne, she trained at Box Hill Institute and then perfected her pastry skills at William Angliss Institute. She loves mixing classic Australian flavors with fresh ideas to keep cooking fun and stress‑free.
Jenna Hartley
Founder & Recipe Creator
Expertise
Education
Box Hill Institute, Melbourne
William Angliss Institute, Melbourne
Jenna is the heart of Picture Perfect Meals, turning simple ingredients into beautiful, easy‑to‑make dishes.
Growing up around family meals in Melbourne, she trained at Box Hill Institute and then perfected her pastry skills at William Angliss Institute. She loves mixing classic Australian flavors with fresh ideas to keep cooking fun and stress‑free.