There is something undeniably joyful about combining juicy pineapple, sweet maraschino cherries, and buttery sugar cookie dough into a delightful treat, and that’s exactly what makes the Pineapple Upside Down Sugar Cookies Recipe such a showstopper. Imagine the classic charm of pineapple upside down cake transformed into bite-sized sugar cookies, each with a golden base and a tropical burst of fruit that dances on your tongue. Whether you’re craving a fun party dessert or a nostalgic twist on classic cookies, this recipe will bring cheer and sunshine to any day with its vibrant flavors and easy preparation.
Ingredients You’ll Need
These ingredients are straightforward and pantry-friendly, yet each one plays a vital role in building the perfect balance of flavor, texture, and color that makes the Pineapple Upside Down Sugar Cookies Recipe so unique and delicious.
- 1 roll (16.5 ounces) refrigerated sugar cookie dough: Provides a buttery, soft base that bakes to a perfect golden finish.
- 1/3 cup brown sugar: Adds a rich, caramel-like sweetness that complements the fruit.
- 2 tablespoons unsalted butter, melted: Helps the brown sugar caramelize beautifully and ensures moist cookie bottoms.
- 12 maraschino cherries, halved: Offers a bright, sweet pop of color and flavor right in the center of each cookie.
- 1/2 cup crushed pineapple, well drained: Brings a juicy tropical zing that balances sweetness and adds texture.
How to Make Pineapple Upside Down Sugar Cookies Recipe
Step 1: Prepare Your Baking Setup
Start by preheating your oven to 350°F. Lightly grease a standard 12-cup muffin tin so that your cookies don’t stick and can easily flip out once baked. This ensures clean, beautiful edges on each cookie and helps achieve that classic pineapple upside down presentation.
Step 2: Create the Caramel Base
In a small bowl, whisk together the melted butter and brown sugar until combined. This luscious mixture will form the caramel-like layer at the bottom, infusing each cookie with deep sweetness and a hint of richness that’s absolutely irresistible.
Step 3: Build the Fruity Layers
Take about 1 teaspoon of the brown sugar mixture and spoon it evenly into the bottom of each muffin cup. Then place a halved maraschino cherry right in the center. Surround this cherry with about 2 teaspoons of well-drained crushed pineapple, carefully keeping the fruit contained so it won’t overflow when baked.
Step 4: Add the Cookie Dough
Unroll your sugar cookie dough and cut it into 12 even pieces. Gently flatten each piece slightly before placing it on top of the pineapple and cherry layer in each muffin cup. This dough acts like a tender lid that bakes golden and adds the perfect cookie chewiness to contrast the juicy fruit underneath.
Step 5: Bake to Perfection
Pop your filled muffin tin into the oven and bake for 12 to 15 minutes. You’re looking for golden edges on the cookie dough as the sign that they’re ready. The smell will be divine, filling your kitchen with buttery sweetness and hints of tropical fruit.
Step 6: Cool and Invert
Allow the cookies to cool in the pan for about 5 minutes. Then, run a knife gently around the edges of each muffin cup to loosen the cookies. Carefully flip the tin over onto a wire rack or tray so the pineapple and cherries sit on top, showcasing that iconic upside down look. Serve warm or at room temperature — either way, they’re fantastic!
How to Serve Pineapple Upside Down Sugar Cookies Recipe
Garnishes
To elevate the presentation, consider adding a light dusting of powdered sugar or a small dollop of whipped cream on each cookie. You can also sprinkle finely chopped toasted coconut around the edges to amplify the tropical vibe.
Side Dishes
These cookies pair beautifully with a scoop of vanilla ice cream for a simple dessert or a refreshing fruit salad featuring mango and kiwi to complement the pineapple flavors. A cup of hot tea or chilled lemonade also balances their sweetness perfectly.
Creative Ways to Present
For a party or special occasion, serve your Pineapple Upside Down Sugar Cookies Recipe on a pretty tiered platter with fresh mint leaves scattered around for freshness and color. You can even drizzle a little caramel sauce over the top for an extra touch of indulgence that will wow your guests.
Make Ahead and Storage
Storing Leftovers
To keep your cookies fresh, store them in an airtight container at room temperature. They will stay delicious for up to three days, maintaining that perfect balance of soft cookie and juicy pineapple.
Freezing
If you want to save them longer, wrap each cookie individually in plastic wrap and place them in a freezer-safe container. Frozen cookies can last up to two months, making them a great make-ahead treat for any occasion.
Reheating
Warm the cookies gently in the oven at 300°F for about 5 minutes to revive their softness and bring back that freshly baked feeling. Avoid microwaving, which can sometimes make the texture less ideal.
FAQs
Can I use homemade sugar cookie dough for this recipe?
Absolutely! While refrigerated dough is convenient, homemade sugar cookie dough works beautifully and allows you to customize flavors or reduce additives.
How important is it to drain the pineapple thoroughly?
Draining the pineapple very well is essential to prevent soggy cookie bottoms and ensure the caramel base stays intact, giving you that perfect texture every time.
Can I substitute maraschino cherries with fresh cherries?
Fresh cherries can be used but will alter the flavor and texture slightly. Maraschino cherries are sweeter and more colorful, making them ideal for this recipe’s classic presentation.
What is the best way to invert cookies without breaking them?
Cool the cookies for a few minutes in the pan, then carefully run a knife around the edges to loosen. Flip the pan gently onto a wire rack and lift it off slowly to keep the cookies intact.
Are these cookies suitable for vegetarians?
Yes! This Pineapple Upside Down Sugar Cookies Recipe uses ingredients that are vegetarian-friendly, making it a sweet treat for many dietary preferences.
Final Thoughts
If you’re looking for a fun, tropical twist on traditional cookies that will bring smiles and delight with every bite, you simply must try this Pineapple Upside Down Sugar Cookies Recipe. It’s easy, charming, and bursting with flavor — a treat that’s perfect for sharing with friends or enjoying any time you want a touch of sunshine in your day.
Print
Pineapple Upside Down Sugar Cookies Recipe
- Prep Time: 10 minutes
- Cook Time: 15 minutes
- Total Time: 25 minutes
- Yield: 12 cookies
- Category: Dessert
- Method: Baking
- Cuisine: American
- Diet: Vegetarian
Description
These Pineapple Upside Sugar Cookies combine the tropical flavors of pineapple and maraschino cherries with classic sugar cookie dough for a fun and fruity dessert. Featuring a gooey brown sugar and butter base topped with juicy pineapple and cherries, these easy-to-make cookies are baked in a muffin tin and inverted for a stunning presentation perfect for parties or everyday treats.
Ingredients
Cookie Base
- 1 roll (16.5 ounces) refrigerated sugar cookie dough
Topping
- 1/3 cup brown sugar
- 2 tablespoons unsalted butter, melted
- 12 maraschino cherries, halved
- 1/2 cup crushed pineapple, well drained
Instructions
- Prepare Oven and Pan: Preheat the oven to 350°F and lightly grease a standard 12-cup muffin tin to prevent sticking.
- Mix Butter and Sugar: In a small bowl, combine the melted butter and brown sugar until well blended, creating a sweet base for the cookies.
- Add Toppings to Muffin Cups: Spoon about 1 teaspoon of the brown sugar and butter mixture into the bottom of each muffin cup. Place half a maraschino cherry in the center of each, then add approximately 2 teaspoons of well-drained crushed pineapple around the cherry for a tropical flavor burst.
- Prepare Cookie Dough: Cut the sugar cookie dough into 12 equal portions, slightly flatten each to create a disc that will fit atop the fruit mixture in each muffin cup.
- Assemble Cookies: Place each flattened dough piece over the pineapple and cherry mixture in the muffin cups, covering the fruit base completely.
- Bake: Bake for 12 to 15 minutes, or until the cookie edges are golden and the cookie is cooked through.
- Cool and Invert: Let the cookies cool in the pan for about 5 minutes, then run a knife around the edges to loosen them. Carefully invert the muffin tin onto a wire rack or tray to release the upside-down pineapple topping and reveal the caramelized brown sugar layer.
- Serve: Serve the cookies warm or at room temperature for the best flavor and texture experience.
Notes
- Drain the pineapple thoroughly to avoid soggy cookie bottoms.
- These cookies are perfect for parties or as a fun tropical twist on classic sugar cookies.
- For easier removal, greasing the muffin tin well or using nonstick spray is recommended.
- Use a sharp knife to loosen edges carefully before inverting to maintain cookie shape.
