Irresistible Pineapple Upside Down Sugar Cookies Recipe

Sweet memories of childhood desserts dance through my classic pineapple upside down sugar cookies, beckoning you to a nostalgic culinary journey.

Bright yellow rings nestled against golden-brown backdrops create an irresistible visual symphony.

Caramelized edges hint at deep flavor complexity waiting to surprise you.

Soft cookie foundations carry delicate tropical notes that spark instant comfort.

Tender crumbs melt seamlessly with candied fruit surfaces, promising decadent sensations.

Subtle butterscotch undertones weave magic into each carefully crafted bite.

Whip up these delightful treats and let pure joy fill your kitchen.

Reasons Pineapple Upside Down Sugar Cookies Delight

• Whip Up Tropical Delight: Transform classic sugar cookies into a fun, fruity treat that brings a burst of pineapple sunshine to your dessert table.
• Simplify Baking Adventure: Create gourmet-looking cookies with minimal effort using a muffin tin, making the process foolproof for bakers of all skill levels.
• Charm Guests with Impressive Presentation: Serve up individual, beautifully caramelized cookies that look like they came from a professional bakery, guaranteed to wow family and friends.
• Customize with Ease: Swap cherries or experiment with different fruit toppings to make this recipe uniquely yours, adding a personal touch to a classic dessert.

Must-Have Ingredients for Pineapple Sugar Cookies

• Pineapple Slices: Sweet and tangy fruit that creates a classic tropical topping for the cookies.
• Maraschino Cherries: Bright red cherries that add a pop of color and sweet flavor to the dessert.
• Butter: Rich dairy ingredient that provides moisture and helps create a tender cookie texture.
• Granulated Sugar: Sweetens the cookie and helps create a crisp exterior.
• Brown Sugar: Adds depth of flavor and helps create a caramel-like bottom for the cookies.

• All-Purpose Flour: Provides structure and helps bind the cookie ingredients together.
• Salt: Enhances the overall flavor of the cookies.
• Baking Soda: Helps the cookies rise and creates a light, soft texture.

• Egg: Binds the ingredients and adds richness to the cookie dough.
• Vanilla Extract: Provides a warm, classic flavor that complements the pineapple and cherry.

Instructions for Pineapple Upside Down Sugar Cookies

Step 1: Prepare Baking Pan

Grab a muffin tin and create a delicious caramel base.

Melt butter and blend with brown sugar.

Spoon this sweet mixture into each muffin compartment.

Carefully place a vibrant pineapple slice and a bright maraschino cherry on top of the caramel layer.

Step 2: Create Creamy Cookie Base

In a spacious mixing bowl, whip granulated sugar and softened butter until they transform into a light, fluffy cloud.

Introduce an egg and vanilla extract, blending until smooth and velvety.

Step 3: Mix Dry Ingredients

• All-purpose flour
• Salt
• Baking soda

Slowly incorporate these dry ingredients into the wet mixture, stirring until completely combined.

Step 4: Shape Cookie Tops

Roll the cookie dough into small balls.

Softly flatten each ball and place directly on top of the pineapple and cherry in each muffin compartment.

Step 5: Bake to Golden Perfection

Slide the muffin tin into a preheated oven at 350°F.

Bake for 14-16 minutes until cookies turn a beautiful golden brown color.

Step 6: Cool and Serve

Allow cookies to rest in the muffin tin for 5 minutes.

Carefully remove each cookie, revealing the stunning upside-down pineapple design.

Let cool completely before serving these tropical treats.

Pineapple Cookie Tips for Juicy, Sweet Results

• Use room temperature butter and egg for smoother, more even mixing and better cookie texture.
• Position maraschino cherries carefully in the center of each pineapple slice for a picture-perfect presentation.
• Spray muffin tin with cooking spray before adding butter and brown sugar mixture to ensure easy cookie removal.
• Store cooled cookies in an airtight container with a slice of bread to keep them soft and prevent drying out.
• Substitute all-purpose flour with a gluten-free blend for those with wheat sensitivities, maintaining the same delicious flavor profile.

New Takes for Pineapple Upside Down Sugar Cookies

• Gluten-Free Pineapple Delight: Replace all-purpose flour with gluten-free flour blend, ensuring a celiac-friendly cookie that maintains the classic caramelized pineapple flavor.
• Vegan Tropical Treat: Swap butter with coconut oil, use a flax egg instead of regular egg, and select plant-based margarine to create a dairy-free, egg-free version of the classic cookie.
• Reduced Sugar Option: Use sugar substitute like stevia or monk fruit sweetener, and opt for fresh pineapple chunks instead of maraschino cherries to decrease overall sugar content while keeping the cookie's delicious essence.
• Coconut Tropical Remix: Add shredded coconut to the cookie dough and sprinkle toasted coconut flakes on top after baking for an extra tropical-inspired texture and flavor profile.

How to Serve Pineapple Sugar Cookies Creatively

• Tropical Dessert Companion: Pair these cookies with a scoop of coconut ice cream for a creamy, tropical twist that enhances the pineapple flavor.
• Brunch Showstopper: Serve alongside fresh mimosas or a light cappuccano, creating a delightful morning treat that will impress breakfast guests.
• Party Platter Perfection: Arrange cookies on a wooden board with fresh mint leaves and additional maraschino cherries for a stunning visual presentation that screams summer celebration.
• Afternoon Tea Delight: Create a small cookie tower with these upside-down treats, complemented by a refreshing passion fruit or mango tea for an elegant afternoon snack.

Keeping Pineapple Sugar Cookies Fresh All Week

• Store cooled cookies in an airtight container lined with parchment paper. Keep in the refrigerator for up to 5 days to maintain freshness and prevent moisture loss.
• Wrap individual cookies tightly in plastic wrap, then place in a freezer-safe container. Freeze for up to 3 months for longer storage. Ensure complete seal to prevent freezer burn.
• Keep cookies in a sealed container at room temperature for 2-3 days. Place a piece of bread inside to help maintain moisture and softness.
• Warm refrigerated or thawed cookies in the microwave for 10-15 seconds. Alternatively, reheat in a preheated oven at 300F for 3-4 minutes to restore original texture and warmth.

FAQs

• Can I use fresh pineapple instead of canned?

No, canned pineapple slices work best because they’re uniform in size and hold their shape better during baking.

• Do I need a special muffin tin for this recipe?

A standard 12-cup muffin tin works perfectly. Just make sure it’s greased well to prevent sticking.

• How do I know when the cookies are perfectly baked?

Look for golden brown edges and a slightly firm center. The cookies will continue to set as they cool in the tin.

• Can I make these cookies ahead of time?

Yes, you can prepare the dough in advance and refrigerate it for up to 2 days before baking. Just bring it to room temperature before forming the cookies.

Pineapple Upside Down Sugar Cookies Recipe

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4.6 from 13 reviews

• Total Time: 35 minutes
• Yield: 12 1x

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Description

Sweet, buttery pineapple upside down sugar cookies blend classic dessert nostalgia with delightful cookie charm. Caramelized pineapple crowns melt-in-your-mouth sugar cookie bases, promising a tropical twist you’ll savor with pure delight.

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Ingredients

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Main Ingredients:

• 12 pineapple slices (from canned)
• 12 maraschino cherries
• 1 1/2 cups all-purpose flour
• 1 cup granulated sugar
• 1/2 cup unsalted butter, softened
• 1/4 cup unsalted butter, melted

Wet Ingredients:

• 1 large egg
• 1 teaspoon vanilla extract

Baking and Seasoning Ingredients:

• 1/3 cup brown sugar
• 1/4 teaspoon salt
• 1/4 teaspoon baking soda

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Instructions

1. Prepare the oven at 350°F and create a caramel base by mixing melted butter and brown sugar. Distribute this mixture evenly across each muffin tin compartment.
2. Carefully place a pineapple slice atop the caramel mixture, then center a maraschino cherry in the middle of each slice.
3. In a large mixing bowl, thoroughly cream granulated sugar with softened butter until the mixture becomes light and airy. Incorporate the egg and vanilla extract, blending until smooth.
4. Separately, combine flour, salt, and baking soda using a whisk, ensuring even distribution of dry ingredients.
5. Gradually fold the dry ingredient mixture into the wet ingredients, stirring until a consistent dough forms.
6. Shape the cookie dough into small rounds, gently flattening each ball before positioning them directly over the pineapple and cherry in the muffin tin.
7. Transfer the muffin tin to the preheated oven and bake for 14-16 minutes, watching for a golden-brown color indicating doneness.
8. After removing from the oven, allow cookies to rest in the tin for 5 minutes, which helps set the caramel and prevents breaking.
9. Carefully extract the cookies from the tin, inverting them to showcase the beautiful caramelized pineapple topping.

Notes

• Perfectly caramelize the brown sugar and butter mixture by ensuring even distribution in each muffin tin compartment for a rich, gooey base.
• Use room temperature ingredients like butter and egg to achieve a smoother, more consistent cookie dough that blends easily and bakes evenly.
• Prevent sticking by generously greasing the muffin tin or using non-stick cooking spray before adding the pineapple and cherry base.
• Try alternative fruits like peaches or mandarin oranges for a creative twist on the classic pineapple upside-down cookie, catering to different taste preferences.

• Prep Time: 20 minutes
• Cook Time: 15 minutes
• Category: Desserts, Snacks
• Method: Baking
• Cuisine: American

Nutrition

• Serving Size: 12
• Calories: 163 kcal
• Sugar: 14 g
• Sodium: 79 mg
• Fat: 7 g
• Saturated Fat: 4 g
• Unsaturated Fat: 3 g
• Trans Fat: 0 g
• Carbohydrates: 23 g
• Fiber: 0.4 g
• Protein: 1.5 g
• Cholesterol: 18 mg