Pineapple Upside-Down Sugar Cookies Recipe

If you’re searching for a delightful twist on classic treats, this Pineapple Upside-Down Sugar Cookies Recipe is about to become your new obsession. Imagine the sweet, caramelized richness of pineapple upside-down cake transformed into a perfectly chewy, buttery sugar cookie — it’s a tropical vacation for your taste buds wrapped in every bite. These cookies blend the nostalgic flavors of browned butter and brown sugar with juicy pineapple rings and bright maraschino cherries, creating a slice of sunshine that’s as fun to make as it is to eat.

Ingredients You’ll Need

Every ingredient in this recipe plays a starring role, coming together to create those perfect textures and flavors you’ll love. From the creamy softened butter that builds the cookie’s richness to the tangy pineapple slices that bring a burst of tropical sweetness, each element is essential.

• 1 cup unsalted butter, softened: Gives the cookies a tender, melt-in-your-mouth base and richer flavor when combined correctly.
• 1 cup granulated sugar: Adds sweetness and helps create the cookie’s chewy texture.
• 1 large egg: Binds all ingredients together and provides moisture for soft cookies.
• 1 teaspoon vanilla extract: Adds warmth and depth to the flavor profile.
• 2 ½ cups all-purpose flour: The foundation for structure, ensuring the cookies hold shape while staying soft.
• 1 teaspoon baking powder: Helps the cookies rise gently without too much puff.
• ½ teaspoon baking soda: Boosts leavening and contributes to a light, tender crumb.
• ½ teaspoon salt: Balances sweetness and enhances overall flavor.
• 1 can (8 oz) pineapple slices, drained: Provides juicy, tangy fruitiness, giving the cookies their signature pineapple upside-down appeal.
• ¼ cup unsalted butter: For melting with brown sugar to create a luscious caramel topping.
• ½ cup brown sugar, packed: Creates that classic caramel note when melted with butter.
• Maraschino cherries: One for each cookie, adding a pop of color and a sweet finishing touch.

How to Make Pineapple Upside-Down Sugar Cookies Recipe

Step 1: Prepare Your Oven and Baking Sheets

Start by preheating your oven to 350°F (175°C). Line two baking sheets with parchment paper to prevent sticking and make cleanup easier, setting yourself up for effortless baking.

Step 2: Cream Butter and Sugar

In a mixing bowl, beat the softened butter and granulated sugar together until the mixture becomes light, fluffy, and well-aerated. This process usually takes about 3 to 4 minutes and sets the fluffy foundation for your cookies.

Step 3: Add Egg and Vanilla

Next, mix in the egg and vanilla extract until they are fully combined. These ingredients add moisture and subtle aromatic flavor that elevate the cookie dough.

Step 4: Mix Dry Ingredients

In a separate bowl, whisk together the all-purpose flour, baking powder, baking soda, and salt. This ensures the leavening agents are evenly distributed for a perfect rise.

Step 5: Combine Wet and Dry Elements

Gradually add the dry ingredient mixture to the creamed butter and sugar, mixing gently until just combined. Overmixing can toughen the dough, so a light hand is key.

Step 6: Create the Caramel Base

In a small saucepan over medium heat, melt ¼ cup of unsalted butter with the brown sugar, stirring until the mixture bubbles and becomes smooth. This caramel sauce is essential for recreating the classic pineapple upside-down flavor.

Step 7: Assemble the Cookies

Spoon about a tablespoon of the warm butter and brown sugar mixture onto each designated cookie spot on your baking sheets. Carefully place one pineapple slice atop each spoonful of caramel.

Step 8: Add Cherry Centers

Gently press one maraschino cherry into the center of every pineapple slice. This vibrant pop of color will make these cookies truly irresistible.

Step 9: Cover with Cookie Dough

Scoop about one tablespoon of cookie dough and carefully spread it over each pineapple slice. Be sure to cover the fruit slightly, leaving some of the pineapple and cherry visible for that beautiful upside-down look.

Step 10: Bake to Perfection

Place the trays in your preheated oven and bake for 12 to 15 minutes, or until the edges of the cookies turn a light golden brown, signaling they are perfectly baked.

Step 11: Cool and Enjoy

Allow the cookies to cool on the baking sheets for about 5 minutes to let the caramel set, then transfer them to a wire rack for complete cooling. This helps maintain their shape and texture.

How to Serve Pineapple Upside-Down Sugar Cookies Recipe

Garnishes

For a simple yet elegant touch, sprinkle a bit of finely shredded toasted coconut or finely chopped toasted pecans around the cookies before serving. These add extra texture and a delightful contrast to the sweetness. A light dusting of powdered sugar right before serving also adds a lovely visual appeal.

Side Dishes

Pair these cookies with a scoop of vanilla bean ice cream or a dollop of whipped cream for a dessert experience that’s both refreshing and decadent. Alternatively, a cup of hot tea or a tropical fruit smoothie complements the pineapple flavor beautifully.

Creative Ways to Present

Serve these cookies on a vibrant tropical-themed platter with fresh pineapple wedges and mint leaves for a festive vibe. You can also stack them into cute cookie towers tied with a bright ribbon for gifting or parties. These charming touches will surely impress everyone!

Make Ahead and Storage

Storing Leftovers

Keep any leftover Pineapple Upside-Down Sugar Cookies in an airtight container at room temperature for up to 4 days. This preserves their softness and the juicy pineapple topping without drying out.

Freezing

To freeze, place cooled cookies in a single layer on a baking sheet and freeze until solid. Then transfer them to a freezer-safe container or zip-lock bag. You can store them for up to 2 months and enjoy a tropical treat anytime.

Reheating

For the best flavor and texture, gently warm frozen cookies in a 300°F oven for 5 to 7 minutes. This quick heat-up brings back the cookie’s softness and slightly reheats the caramel topping without burning.

FAQs

Can I use fresh pineapple instead of canned?

Absolutely! Fresh pineapple rings work beautifully if you drain them well and pat dry. Just ensure they’re not too juicy to avoid soggy cookies.

What can I substitute for maraschino cherries?

If you prefer a different flavor or want to avoid the bright red color, try using glazed or preserved cherries, or even halved fresh cherries. Just make sure they hold their shape during baking.

How do I prevent the caramel from burning?

Keep the heat medium and stir continuously when melting the butter and brown sugar. Removing from heat as soon as the mixture is bubbling and smooth will prevent burning.

Can I make these cookies gluten-free?

Yes! Substitute all-purpose flour with a 1:1 gluten-free flour blend that contains xanthan gum for the best texture. The cookies will still be deliciously tender.

Why are my cookies flat instead of thick?

Make sure your butter is softened but not melted when creaming with sugar. Also, avoid overmixing the dough after adding flour, as too much mixing can cause cookies to spread thin.

Final Thoughts

This Pineapple Upside-Down Sugar Cookies Recipe is a joyful celebration of classic flavors reimagined into a handheld delight. Whether you’re baking for a party or just craving a sweet tropical treat, these cookies are sure to brighten your day and captivate your guests. Grab your ingredients, invite a friend to bake along, and enjoy every delightful bite!

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