Irresistible Pineapple Upside-Down Sugar Cookies Recipe

Sweet memories often bloom from unexpected pineapple upside-down sugar cookies that spark childhood joy.

Golden-edged treats with caramelized fruit nestled perfectly atop buttery dough.

Soft patches of sunny yellow shine through each delicate cookie surface.

Tropical hints dance across your taste buds, promising delightful surprises in every bite.

Crumbly textures mingle with rich, gooey fruit centers that whisper classic dessert nostalgia.

Baking these treasures feels like capturing a moment of pure culinary magic.

Grab your mixing bowl and start creating delectable memories that will make everyone smile.

What You Need For Pineapple Upside-Down Sugar Cookies

• Butter, Brown Sugar: Sweet caramel-like base that creates a sticky, rich foundation for the cookie.
• Pineapple Chunks, Maraschino Cherries: Classic tropical fruit topping that adds vibrant color and tangy sweetness.

• All-Purpose Flour: Standard baking flour for creating a tender, soft cookie texture.
• Granulated Sugar, Brown Sugar: Provides sweetness and helps with cookie structure and moisture.
• Baking Powder: Helps cookies rise and become light and fluffy.
• Salt: Enhances overall flavor and balances sweetness.

• Eggs: Binding agent that helps hold the cookie dough together.
• Vanilla Extract: Adds warm, classic bakery flavor to the cookie base.
• Vegetable Oil or Melted Butter: Provides moisture and helps create a soft cookie texture.

How To Bake Pineapple Upside-Down Sugar Cookies The Easy Way

Step 1: Prepare Baking Station

Warm up the oven to 350 degrees Fahrenheit (175 degrees Celsius). Grab a muffin tin and give it a light spray with non-stick cooking spray, ensuring every cup is perfectly coated.

Step 2: Create Caramel Base

In a cozy mixing bowl, blend melted butter with rich 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 for your cookies.

Step 3: Arrange Fruity Decorations

Lovingly place your pineapple pieces into the cups, creating a beautiful mosaic. Carefully nestle a vibrant maraschino cherry half into each cup, making sure they sit prettily atop the caramel base.

Step 4: Mix Cookie Dough

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

Stir everything together until a smooth, creamy dough forms.

Step 5: Fill the Cups

Spoon the cookie dough carefully over the pineapple and cherry arrangement. Make sure to cover the fruity base completely but don’t overfill the cups.

Step 6: Bake to Perfection

Slide the muffin tin into the preheated oven. Bake for about 18-20 minutes, watching for a golden-brown top that signals cookie deliciousness.

Step 7: Flip and Reveal

Once baked, remove from the oven and let cool for just a few minutes. Carefully invert the muffin tin onto a serving plate, allowing the cookies to release with their beautiful fruity tops facing up.

Serving Tip: Enjoy these cookies warm, when the caramel is still gooey and the flavors are at their peak. They’re perfect with a cup of coffee or as a sweet afternoon treat!

Smart Tips For Pineapple Upside-Down Sugar Cookies

• Customize Caramelization: Adjust the brown sugar and butter ratio for a deeper, richer caramel flavor that coats the pineapple perfectly.
• Boost Fruit Freshness: Use fresh, ripe pineapple chunks for the most vibrant and juicy taste in your cookies.
• Prevent Sticking Tricks: Ensure you generously spray the muffin tin to guarantee easy cookie removal without breaking.
• Experiment with Variations: Swap cherries with other fruits like mandarin oranges or berries for a unique twist on the classic recipe.
• Temperature Control: Let the cookies cool slightly in the muffin tin before inverting to help them set and maintain their beautiful shape.

How To Store And Reheat Pineapple Upside-Down Sugar Cookies

• Refrigerate: Store leftover cookies in an airtight container, layering between parchment paper to prevent sticking, and keep chilled for up to 3 days.
• Freeze: Wrap individual cookies tightly in plastic wrap, then place in a freezer-safe container to preserve freshness for 2-3 weeks.
• Warm Gently: Reheat refrigerated cookies in the microwave for 10-15 seconds or in a preheated oven at 300F for 3-4 minutes to restore their soft texture.
• Room Temperature: Allow frozen cookies to thaw naturally at room temperature for about 30 minutes before serving for the best taste and texture.

What Pairs Well With Pineapple Upside-Down Sugar Cookies

• Pair with Tropical Rum Cocktail: Sip on a light, refreshing rum punch that echoes the pineapple's sweet tropical notes. The cocktail's citrusy undertones will complement the caramelized brown sugar in the cookies.
• Match with Coconut Vanilla Ice Cream: Scoop creamy coconut vanilla ice cream alongside these cookies for a dreamy dessert combination. The cool, smooth texture balances the warm, sticky-sweet cookie perfectly.
• Enjoy with Iced Hawaiian Coffee: Brew a smooth, medium-roast Hawaiian coffee served over ice. Its subtle nutty flavor and slight sweetness will enhance the caramelized pineapple and cherry elements in the cookies.
• Complement with Butterscotch Liqueur: Drizzle a small amount of butterscotch liqueur over the cookies or serve as a side sip. The rich, buttery notes will intensify the brown sugar and fruit flavors in this delightful treat.

Fun Variations Of Pineapple Upside-Down Sugar Cookies

• Tropical Fruit Fusion: Swap pineapple chunks with mango or papaya pieces for a different island-inspired flavor profile.
• Caramel Nutty Crunch: Sprinkle chopped pecans or macadamia nuts over the fruit before adding the cookie dough for extra texture and richness.
• Berry Burst Edition: Replace pineapple and cherries with mixed berries like raspberries, blueberries, and strawberries for a tangy, colorful alternative.
• Spiced Coconut Remix: Incorporate shredded coconut and a pinch of cinnamon into the brown sugar mixture to create a warm, aromatic cookie variation.

FAQs About Pineapple Upside-Down Sugar Cookies

• 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 tin.

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

A standard muffin tin is all you need. If you don’t have one, you can use a mini cake pan or specialized cookie pan with individual wells.

• Are these cookies good for parties or gatherings?

Absolutely! These cute, individual-sized cookies are great for potlucks, brunches, and dessert tables. They’re easy to serve and look impressive with their caramelized fruit topping.

• Can I make these cookies ahead of time?

Yes, you can prepare the ingredients in advance and assemble the cookies just before baking. They’re best served warm, but can be stored at room temperature for a day or two after baking.

Why Pineapple Upside-Down Sugar Cookies Are So Much Fun

• Caramelize Sweet Surprises: These cookies transform classic upside-down cake flavors into bite-sized treats, delivering a rich caramel and fruity punch in every single morsel.
• Simplify Baking Magic: The muffin tin method makes creating these elegant desserts super easy, allowing even novice bakers to craft professional-looking treats without complicated techniques.
• Customize Flavor Adventure: Pineapple chunks and bright red cherries create a playful tropical twist, turning standard sugar cookies into a delightful dessert that feels like a mini vacation on your taste buds.
• Perfectly Portioned Pleasure: Individual cookie servings mean no messy cutting, easy sharing, and cute presentation that will impress family and friends at potlucks, brunches, or casual gatherings.

Pineapple Upside-Down Sugar Cookies Recipe

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4.6 from 31 reviews

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

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Description

Delightful Pineapple Upside-Down Sugar Cookies blend classic dessert charm with nostalgic comfort. Caramelized pineapple crowns buttery sugar cookies, promising a sweet escape that tempts taste buds with each delectable bite.

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Ingredients

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Main Ingredients:

• 1 can pineapple rings (fresh or canned)
• ½ cup maraschino cherries
• ½ cup unsalted butter
• ½ cup brown sugar

Dry Ingredients:

• 2 cups all-purpose flour
• 1 teaspoon baking powder
• ¼ teaspoon salt

Wet Ingredients:

• ½ cup unsalted butter, softened
• ¾ cup granulated sugar
• 1 large egg
• 1 teaspoon vanilla extract

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Instructions

1. Prepare the muffin tin by generously coating each cavity with non-stick spray to ensure easy cookie removal.
2. Create a caramelized base by whisking melted butter and brown sugar into a smooth, glossy mixture that will infuse rich flavor into the cookies.
3. Carefully distribute the butter-sugar blend across the bottom of each muffin cup, ensuring an even layer that will caramelize during baking.
4. Artfully arrange tropical pineapple chunks and vibrant maraschino cherries in a decorative pattern within each cup, positioning them strategically to create an appealing visual design.
5. The placement of fruit should be intentional, with pieces nestled gently against the sides and bottom of the muffin tin to create a stunning presentation when the cookies are inverted.
6. Proceed with adding the cookie dough carefully over the fruit layer, making sure not to disturb the carefully arranged tropical ingredients underneath.

Notes

• Use room temperature butter for easier mixing and smoother texture in the sugar-butter base.
• Drain pineapple chunks thoroughly to prevent excess moisture from making cookies soggy.
• For a caramel-like finish, let the brown sugar and butter mixture slightly caramelize before adding fruit.
• Experiment with different fruits like mandarin oranges or peaches as delightful alternatives to pineapple.

• 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: 6 g
• Saturated Fat: 3 g
• Unsaturated Fat: 2 g
• Trans Fat: 0 g
• Carbohydrates: 22 g
• Fiber: 1 g
• Protein: 2 g
• Cholesterol: 30 mg