Heavenly Pineapple Upside-Down Sugar Cookies Recipe for Spring

Sweet memories of childhood summers dance through my mind when I think about this delightful pineapple upside-down sugar cookies creation.

Nostalgic flavors blend perfectly in every golden-edged morsel.

Caramelized fruit nestles atop buttery dough, promising a delectable treat.

Soft and chewy textures promise pure comfort in each bite.

Tropical hints of sunshine burst through familiar cookie goodness.

Baking these treats feels like wrapping yourself in warm, sweet memories.

You’ll want to savor every crumb of this delightful dessert.

Best Pairings for Pineapple Upside-Down Sugar Cookies

• Pair these sweet cookies with a refreshing piña colada, bringing out the pineapple's tropical essence and complementing the caramelized brown sugar notes.
• Serve alongside a smooth vanilla latte or cappuccino, whose rich, creamy texture balances the cookie's sweet and tangy profile perfectly.
• Drizzle a small amount of dark rum over the cookies to enhance the caramelized flavors and add depth to the dessert's taste experience.
• Follow the cookies with a zesty lemon or passion fruit sorbet to cut through the sweetness and provide a refreshing contrast.

What Makes Pineapple Upside-Down Sugar Cookies Addictive

• Baked in a muffin tin, these individual-sized cookies ensure everyone gets a perfectly portioned serving with caramelized fruit topping.
• Transform the classic pineapple upside-down cake into a handheld cookie, bringing a playful and modern spin to a traditional dessert that sparks childhood memories.
• Minimal ingredients and simple steps make this recipe accessible for bakers of all skill levels, from beginners to seasoned home cooks.

What You’ll Need to Bake Pineapple Upside-Down Sugar Cookies

• Butter: Provides rich flavor and helps create the caramel-like base.
• Brown Sugar: Creates a sweet, sticky caramel layer that will coat the bottom of the cookies.

• Pineapple Chunks: Adds tropical sweetness and moisture to the cookie base.
• Maraschino Cherries: Brings a pop of color and classic retro dessert flavor.

• All-Purpose Flour: The primary structure for the cookie, providing texture and stability.
• Granulated Sugar: Adds sweetness and helps with cookie browning.
• Baking Powder: Ensures the cookies rise and become light and fluffy.
• Salt: Enhances overall flavor and balances the sweetness.
• Eggs: Bind the ingredients and provide structure to the cookies.
• Vanilla Extract: Adds depth and classic baking flavor.
• Milk: Helps create a smooth, consistent cookie dough.

• Non-Stick Cooking Spray: Ensures easy removal of cookies from the muffin tin.

Putting Together Pineapple Upside-Down Sugar Cookies

Step 1: Warm Up the Oven

Crank the oven to a toasty 350°F (175°C). Grab your muffin tin and give it a quick spritz of non-stick cooking spray to prevent any sticky situations.

Step 2: Create the Caramel Base

In a cozy little bowl, blend melted butter with brown sugar until they become best friends. Gently spoon about a teaspoon of this golden mixture into the bottom of each muffin cup, creating a sweet foundation.

Step 3: Arrange Fruity Goodness

Time to get artistic! Carefully place pineapple chunks and a half maraschino cherry into each cup. Arrange them with care, like you’re creating a mini edible masterpiece. Make sure the fruits nestle nicely into the buttery-sugary base.

Step 4: Prepare the Cookie Dough

• All-purpose flour
• Granulated sugar
• Unsalted butter
• Eggs
• Vanilla extract
• Baking powder
• Salt

Grab a mixing bowl and combine these ingredients until you have a smooth, delightful cookie dough that’s ready to transform into something magical.

Step 5: Top the Fruits

Scoop small portions of cookie dough and gently place them over the arranged pineapple and cherries. Press down lightly to ensure the dough covers the fruits completely.

Step 6: Bake to Perfection

Slide the muffin tin into the preheated oven. Bake for about 15-18 minutes, or until the cookie tops turn a beautiful golden brown and look irresistibly tempting.

Step 7: Cool and Flip

Once baked, let the cookies rest in the tin for a few minutes. Then, carefully invert the tin onto a serving plate. The cookies will release with their fruity caramel topping facing up, creating a stunning dessert that’ll make everyone’s mouth water.

Tips to Nail the Texture in Pineapple Upside-Down Sugar Cookies

• Caramelize with Care: Spread the butter and brown sugar mixture evenly to create a perfect golden-brown base that won't stick to the pan.
• Choose Fresh Pineapple: Opt for ripe, juicy pineapple chunks to enhance the natural sweetness and add a vibrant flavor to your cookies.
• Drain Fruit Thoroughly: Pat pineapple and cherries dry before placing them in the muffin cups to prevent excess moisture from making the cookies soggy.
• Customize Your Toppings: Experiment with different fruits like peaches or mangoes for a unique twist on the classic pineapple upside-down cookie.
• Serve at Room Temperature: Let the cookies cool slightly before removing from the tin to ensure they hold their shape and caramelized topping.

How to Store and Refresh These Cookies Later

• Store cooled cookies in an airtight container for up to 3 days, separating layers with parchment paper to prevent sticking.
• Wrap individual cookies tightly in plastic wrap, then place in a freezer bag. Freeze for up to 2 months for best quality.
• Remove cookies from freezer and let sit at room temperature for 30 minutes before serving. Avoid microwaving to maintain texture.
• Warm gently in a preheated 300F oven for 5-7 minutes to restore slight crispness and bring out the caramelized flavor.

Tweak Your Pineapple Cookies With These Ideas

• Gluten-Free Version: Replace all-purpose flour with a gluten-free blend, ensuring the same texture and taste for those with wheat sensitivities.
• Vegan Adaptation: Swap butter with coconut oil, use plant-based egg replacer, and select dairy-free maraschino cherries to create a completely animal-product-free cookie.
• Low-Sugar Alternative: Substitute brown sugar with monk fruit sweetener or stevia, reducing overall sugar content while maintaining a caramelized flavor profile.
• Tropical Fruit Swap: Replace pineapple with mango or passion fruit chunks for a different exotic fruit experience that still provides a sweet, tangy complement to the cookie base.

Pineapple Sugar Cookies FAQ

• Can I use canned pineapple for this recipe?

Yes, canned pineapple chunks work perfectly. Just make sure to drain them well before adding to the muffin cups to prevent excess moisture.

• Do I need any special equipment to make these cookies?

You’ll need a standard muffin tin and non-stick cooking spray. A regular muffin pan works best for creating individual cookie servings.

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

The cookies are done when the edges turn golden brown and the top springs back lightly when touched, typically around 12-15 minutes of baking.

• Can I substitute maraschino cherries with fresh cherries?

While maraschino cherries are traditional, fresh cherries can work. Just remove the pits and cut them in half before placing in the muffin cups.

Pineapple Upside-Down Sugar Cookies Recipe

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4.8 from 14 reviews

• Total Time: 30 minutes
• Yield: 12 1x

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Description

Tropical paradise meets classic dessert in these irresistible Pineapple Upside-Down Sugar Cookies that blend sweet caramelized pineapple with buttery cookie perfection. Sweet nostalgia and island charm create a delightful treat you’ll savor with each delectable bite.

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Ingredients

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Main Ingredients:

• 1 can or 6–8 fresh pineapple rings
• ½ cup unsalted butter
• ½ cup brown sugar

Flour and Dry Ingredients:

• 1 ½ cups all-purpose flour
• 1 teaspoon (5 grams) baking powder
• ¼ teaspoon salt

Cookie Wet Ingredients:

• ½ cup unsalted butter, softened
• ½ cup granulated sugar
• 1 large egg
• 1 teaspoon vanilla extract
• 4–6 maraschino cherries

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Instructions

1. Prepare the oven environment by warming it to 350F (175C) and thoroughly coating a muffin tin with non-stick spray to prevent potential sticking.
2. Create a rich caramel-like base by whisking melted butter and brown sugar until smooth and well-combined.
3. Distribute the butter-sugar mixture evenly across the muffin tin, carefully spooning approximately one teaspoon into each individual cup.
4. Artfully place pineapple chunks and halved cherries at the bottom of each prepared muffin cavity, ensuring attractive positioning and complete coverage.
5. Position the tin strategically in the preheated oven, allowing the sugary mixture to caramelize and infuse the fruit with deep, golden undertones.
6. Monitor the baking process closely, watching for the edges to turn golden brown and the fruit to become slightly translucent and glossy.
7. Once baked, remove from the oven and let the cookies rest momentarily, allowing the caramelized fruit to set and develop a rich, complex flavor profile.
8. Carefully invert the muffin tin onto a serving platter, gently tapping to release the cookies, revealing the beautifully caramelized fruit topping.
9. Allow the upside-down cookies to cool completely, ensuring the caramel and fruit remain perfectly adhered to the cookie base.

Notes

• Caramelize the brown sugar and butter mixture gently to prevent burning, creating a rich, golden base for the cookies.
• Arrange pineapple chunks and cherries with care, ensuring even distribution and an aesthetically pleasing presentation.
• For a gluten-free version, substitute all-purpose flour with a 1:1 gluten-free baking blend to maintain the cookie’s soft texture.
• Experiment with alternative fruits like peaches or apricots to create unique flavor variations while keeping the classic upside-down cookie concept.

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

Nutrition

• Serving Size: 12
• Calories: 150
• Sugar: 10 g
• Sodium: 150 mg
• Fat: 7 g
• Saturated Fat: 4 g
• Unsaturated Fat: 2 g
• Trans Fat: 0 g
• Carbohydrates: 20 g
• Fiber: 1 g
• Protein: 2 g
• Cholesterol: 30 mg