Name: Pineapple Cookie Delights Recipe
Prep time: 20 min
Cook time: 25 min
Total time: 45 min
Yield: 12
Cuisine: American
Ingredients: 3 cups all-purpose flour; 1 cup butter (room temperature); 1 1/2 cups granulated sugar; 2 eggs; 1/2 cup sour cream; 1 teaspoon baking powder; 1 teaspoon cornstarch; 1/2 teaspoon salt; 2 teaspoons vanilla extract; 1/3 canned pineapple slices; 1/3 maraschino cherries; 1/2 cup melted butter; 1 cup light brown sugar (packed)

Sweet, golden cookies packed with tropical pineapple cookie delights burst with summer memories and homemade comfort.

Tropical fruit transforms ordinary baking into an extraordinary adventure.

Crisp edges and soft centers make these treats irresistible to everyone who tastes them.

Each bite carries a delightful balance of sweetness and tanginess that dances across your palate.

Simple ingredients come together quickly, creating magic in your kitchen.

The aroma of freshly baked pineapple cookies will draw everyone near, eager to sample these delectable treats.

Bake a batch and watch smiles spread with every delicious morsel.

Seal cookies in an airtight container with parchment paper between layers. Keep refrigerated for up to 5-7 days to maintain freshness and prevent moisture buildup.
Wrap each cookie individually in plastic wrap, then place in a freezer-safe container. Freeze for up to 3 months without losing texture or flavor quality.
Warm cookies at 300°F for 3-5 minutes to restore crispy edges and revive soft centers. Use a toaster oven or conventional oven for best results.
Heat cookies for 10-15 seconds on medium power. Check frequently to prevent soggy texture and ensure the brown sugar caramelization remains intact.

FAQs

Can I use fresh pineapple instead of canned pineapple rings?

Fresh pineapple works, but canned pineapple rings are easier to use and provide a more consistent shape for the cookie base.

Do I need any special equipment to make these cookies?

A mini round cake pan or muffin top pan is recommended to create the perfect shape and caramelization of the brown sugar and pineapple.

How do I prevent the cookies from sticking to the pan?

Use a non-stick pan and ensure you spread the brown sugar mixture evenly across the bottom of each cavity before adding pineapple and cookie dough.

Can I make these cookies ahead of time?

Yes, you can prepare the dough in advance and refrigerate it for up to 24 hours before baking. The cookies are best enjoyed within 2-3 days of baking.

Pineapple Upside-Down Cookies: Why They’re a Treat

Transform classic pineapple upside-down cake into adorable mini cookies that burst with tropical sweetness and charm.
Whip up these delectable treats using basic pantry ingredients and minimal kitchen skills, making it perfect for bakers of all levels.
Impress friends and family with these stunning individual desserts that look professionally made but are surprisingly easy to create.
Ideal for potlucks, brunches, dessert tables, and casual gatherings where you want something uniquely delicious that stands out from standard cookies.

Main Ingredients:

Butter: A rich, creamy ingredient that provides moisture and flavor to the cookie dough.
Granulated Sugar: Adds sweetness and helps create a light, crisp texture.
Eggs: Bind the ingredients together and contribute to the cookie's structure.
Flour: The primary dry ingredient that forms the base of the cookie dough.

Flavor Enhancers:

Vanilla Extract: Adds a warm, sweet aroma and depth of flavor to the cookies.
Sour Cream: Provides moisture and helps create a tender, soft cookie texture.
Salt: Balances the sweetness and enhances the overall flavor profile.

Fruit and Topping Ingredients:

Pineapple Slices, Maraschino Cherries: Create a classic upside-down dessert look with sweet, tangy fruit.
Light Brown Sugar: Forms a caramel-like coating that adds richness and moisture to the bottom of the cookies.
Melted Butter: Helps create a smooth, glossy base for the fruit topping.

Additional Dry Ingredients:

Baking Powder, Cornstarch: Help the cookies rise and maintain a soft, tender texture.

Large mixing bowl: Essential for combining ingredients smoothly.
Muffin top pan or mini round cake pan: Crucial for creating perfect cookie shapes.
Cookie scoop: Helps measure consistent dough portions.
Offset spatula: Perfect for evenly spreading cookie dough.
Wax paper: Necessary for catching sticky brown sugar during cooling.
Measuring cups and spoons: Important for accurate ingredient quantities.
Mixing spatula or whisk: Helps blend ingredients thoroughly.

Step 1: Fire Up The Oven

Crank the oven to a toasty 350 degrees Fahrenheit, getting ready for some sweet magic.

Step 2: Select Your Baking Vessel

Grab a mini round cake pan or muffin top pan that’s non-stick and ready for action.

Step 3: Cream Butter And Sugar

In a spacious mixing bowl, whip together butter and granulated sugar until they transform into a fluffy cloud of deliciousness.

Step 4: Introduce Wet Friends

Drop in:

Eggs
Vanilla extract
Sour cream

Blend these buddies until they’re perfectly combined.

Step 5: Welcome Dry Ingredients

Toss in:

Flour
Baking powder
Cornstarch
Salt

Gently mix until the dough just comes together, avoiding overmixing.

Step 6: Craft Caramel Base

In a separate bowl, marry melted butter and light brown sugar into a rich, gooey mixture.

Step 7: Create Sticky Foundation

Splash about a tablespoon of the brown sugar mix into each pan cavity, spreading it to create a complete bottom coating.

Step 8: Arrange Fruity Decoration

Nestle a pineapple slice into the sugary base and plant a maraschino cherry right in its center.

Step 9: Top With Cookie Dough

Plop a hefty 3-tablespoon scoop of cookie dough onto each pineapple slice.

Smooth the surface with an offset spatula.

Step 10: Bake To Perfection

Slide the pan into the oven and bake for 25 minutes.

Watch for golden edges and bubbling brown sugar along the sides.

Step 11: First Cool Down

After baking, let cookies rest for 10 minutes.

Flip them onto wax paper, ready to catch any runaway caramel.

If a pineapple slice gets shy, just guide it back home.

Step 12: Final Chill

Allow cookies to cool completely before diving in.

Step 13: Store With Care

Tuck these treats into an airtight container.

They’ll stay fresh for a week but taste most incredible within 2-3 days.

Prevent Sticking Spray your pan with non-stick cooking spray before adding the brown sugar mixture for easier cookie removal.
Choose Fresh Ingredients Select ripe, vibrant maraschino cherries and fresh pineapple slices to enhance the overall flavor and visual appeal of the cookies.
Control Dough Consistency Ensure cookie dough is slightly chilled before scooping to maintain shape and prevent spreading during baking.
Adjust Sweetness Reduce brown sugar quantity if you prefer less sweetness, or use a sugar substitute for a lighter version of the dessert.
Maximize Freshness Serve cookies slightly warm for the best taste, and store them in a single layer to maintain their crisp texture and prevent sogginess.

Gluten-Free Pineapple Cookies: Replace wheat flour with almond flour or gluten-free blend for celiac-friendly option.
Vegan Tropical Treat: Substitute butter with coconut oil, eggs with flax eggs, and use dairy-free sour cream alternative.
Reduced Sugar Version: Use monk fruit sweetener instead of granulated sugar and replace brown sugar with sugar-free caramel syrup.
Tropical Fruit Swap: Replace pineapple with mango or peach slices for a different fruity experience, maintaining similar baking technique.

Ways to Serve Upside-Down Cookies

Tropical Dessert Plate: Arrange the cookies on a vibrant platter with fresh mint leaves and extra maraschino cherries for a stunning presentation.
Vanilla Ice Cream Companion: Top each warm cookie with a scoop of creamy vanilla ice cream, letting it slightly melt for a decadent treat that combines warm and cold textures.
Coffee or Tea Pairing: Serve these sweet cookies alongside a rich espresso or aromatic Earl Grey tea to balance the sweetness and enhance the pineapple flavor.
Brunch Centerpiece: Include these cookies as a delightful dessert option during weekend brunch gatherings, complementing other fruity and sweet breakfast dishes.

Marcus Reed

Founder & Food Content Creator

Expertise

Single-recipe development, Seasonal and local ingredient utilization, Food photography and styling, Culinary writing and content creation

Education

Culinary Arts Certificate, Blue Ridge Community and Technical College, WV
Focus: Fundamentals of culinary techniques, emphasizing hands-on experience in small-scale kitchen settings.

Marcus’s story begins in Asheville, where good food and family kitchens shaped his earliest memories. After hands-on culinary training and a lot of trial (and a little error), he realized that real cooking isn’t about perfection, it’s about connection.
At Pan and Oven, Marcus crafts recipes that are easy to follow, packed with flavor, and built for real kitchens.

Tropical Pineapple Cookie Delights: A Sweet Sunshine Recipe

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