If you’re in the mood for a cookie that brings a tropical twist with every bite, you’ve absolutely got to try this Irresistibly Gooey Pineapple Upside Down Sugar Cookies Recipe. These cookies combine the classic sweetness of sugar cookies with the juicy, caramelized charm of pineapple rings perched right on top, creating a treat that’s soft, chewy, and bursting with flavor. With a perfect balance of buttery dough and tangy pineapple that turns golden during baking, this recipe turns a simple cookie into an unforgettable indulgence that your family and friends will rave about.
Ingredients You’ll Need
Each ingredient in this recipe is simple but plays a crucial role in creating the perfect texture, sweetness, and tropical flair that makes these cookies stand out. From the rich butter that makes every bite melt in your mouth, to the aromatic vanilla that ties the flavors together perfectly, every component is essential.
- Unsalted Butter (1 cup, softened): Provides richness and a tender crumb for the cookie base.
- Granulated Sugar (1 cup): Sweetens the dough and contributes to the classic sugar cookie texture.
- Large Egg (1): Binds the dough together and adds moisture for softness.
- Vanilla Extract (1 teaspoon): Adds warm, aromatic depth that enhances all flavors.
- All-Purpose Flour (2 cups): Forms the structure of the cookies for perfect chewiness.
- Baking Soda (1 teaspoon): Provides a gentle lift and helps with even browning.
- Salt (1/2 teaspoon): Balances sweetness and intensifies the buttery flavor.
- Canned Pineapple Rings (10-12, well-drained and patted dry): The star of the recipe, adding juicy tropical sweetness that caramelizes beautifully.
- Additional Granulated Sugar (to taste): Sprinkled on top for a sparkling crunch and enhanced sweetness.
How to Make Irresistibly Gooey Pineapple Upside Down Sugar Cookies Recipe
Step 1: Preheat and Prepare
Start by heating your oven to 350°F (180°C). This ensures it’s perfectly hot and ready to work its magic on your cookies. Meanwhile, line your baking trays thoroughly with parchment paper — this will prevent sticking and help your cookies bake evenly.
Step 2: Cream Butter and Sugar
In a large bowl, beat together the softened butter and granulated sugar until you see a fluffy, pale mixture. This usually takes about 2 to 3 minutes and it’s vital because it introduces air, giving the cookies a lovely light texture.
Step 3: Add Egg and Vanilla
Next, stir in the egg and vanilla extract. These ingredients bring moisture and that unmistakable comforting vanilla flavor that makes sugar cookies so addictive. Mix until everything is smoothly combined.
Step 4: Combine Dry Ingredients
In a separate bowl, whisk together the all-purpose flour, baking soda, and salt. This ensures your leavening agent is distributed evenly and your cookies won’t have any annoying lumps or uneven rising.
Step 5: Mix Dry Ingredients into Wet
Slowly incorporate the dry mixture into the wet butter mixture. Using a gentle folding motion helps avoid overworking the dough and keeps your cookies delightfully tender.
Step 6: Scoop Dough and Add Pineapple
Using about 2 tablespoons per cookie, scoop out dough mounds onto your prepared pans, spacing them around 2 inches apart. Now the fun part — gently press one drained and dried pineapple ring on top of each cookie dough mound, slightly flattening the dough beneath.
Step 7: Sprinkle Sugar and Bake
A little extra sprinkle of granulated sugar over each pineapple gives the cookies a sweet crunch and helps caramelize the pineapple during baking. Pop your trays in the oven and bake for 11 to 13 minutes, watching for the edges to turn golden brown while the centers remain soft.
Step 8: Cool and Enjoy
Once baked, let the cookies rest on the tray for a few minutes so they firm up slightly and are easier to handle. Then transfer them to a wire rack to cool completely. This final step preserves that gooey texture that makes this Irresistibly Gooey Pineapple Upside Down Sugar Cookies Recipe so charming.
How to Serve Irresistibly Gooey Pineapple Upside Down Sugar Cookies Recipe
Garnishes
For an elevated touch, consider a light dusting of powdered sugar before serving or a drizzle of honey to add an extra layer of sweetness that complements the pineapple perfectly. Fresh mint leaves can add a surprising yet delightful pop of color and a gentle herbaceous contrast.
Side Dishes
These cookies pair wonderfully with a scoop of vanilla bean ice cream or a dollop of whipped cream, turning a simple cookie into a mini dessert. For a refreshing balance, serve alongside a chilled cup of iced tea or a fruity tropical smoothie.
Creative Ways to Present
Arrange these cookies on a decorative platter lined with pineapple leaves or edible flowers for a festive display at your next gathering. You could even sandwich two cookies together with pineapple cream cheese frosting for a playful twist that guests will adore. The gooey pineapple makes presentation naturally appealing, so little extra effort can go a long way.
Make Ahead and Storage
Storing Leftovers
After enjoying a batch, store leftover cookies in an airtight container at room temperature. They will stay fresh and delicious for up to 3 days, keeping that perfect soft and gooey center intact.
Freezing
To keep these cookies longer, freeze them in a single layer on a baking sheet, then transfer to a zip-top bag or airtight container. Frozen cookies can last up to 3 months. Thaw completely at room temperature when you’re ready to indulge again.
Reheating
If you want that freshly baked warmth, pop your cookies in a preheated oven at 300°F for 5 minutes or microwave for about 15 seconds. Reheating revives the gooey pineapple and soft texture beautifully, almost as if they just came out of the oven for the first time.
FAQs
Can I use fresh pineapple instead of canned?
Absolutely! Fresh pineapple rings work wonderfully but make sure to pat them dry thoroughly so the excess moisture doesn’t affect the cookie dough’s consistency and baking process.
How do I make sure the cookies stay gooey and soft?
Don’t overbake the cookies; keep a close eye during the last few minutes and remove them when the edges are golden but the center is still slightly soft. Also, using softened butter and not chilled dough helps maintain that gooey texture.
Can I substitute the all-purpose flour with gluten-free flour?
Yes, you can use a gluten-free flour blend, but be sure it’s a 1:1 substitute designed for baking. Some blends may alter texture slightly, so adjust baking time if necessary and watch closely.
Is it okay to use pineapple chunks instead of rings?
While pineapple rings create the classic “upside down” look, chunks can be used for a more rustic style. Just be mindful that smaller pieces might caramelize faster, so place them carefully on the dough.
How should I store these cookies if I want to keep them fresh for a party?
Store baked and completely cooled cookies in an airtight container at room temperature. If transporting, layering them with parchment paper helps keep each cookie intact and prevents sticking.
Final Thoughts
This Irresistibly Gooey Pineapple Upside Down Sugar Cookies Recipe is a joyful way to bring sunshine and sweetness into your kitchen. With just a handful of simple ingredients and easy steps, you get a cookie that’s soft, gooey, and bursting with unexpected tropical charm. I truly hope you treat yourself and your loved ones to these delightful cookies — they’ll quickly become a favorite for good reason. Happy baking and even happier tasting!
Print
Irresistibly Gooey Pineapple Upside Down Sugar Cookies Recipe
- Prep Time: 15 minutes
- Cook Time: 13 minutes
- Total Time: 28 minutes
- Yield: 12 cookies
- Category: Dessert
- Method: Baking
- Cuisine: American
Description
These Irresistibly Gooey Pineapple Upside Down Sugar Cookies combine the classic tropical flavors of pineapple with sweet, buttery sugar cookies. Each cookie showcases a juicy pineapple ring pressed into a soft and chewy sugar cookie base, perfectly caramelized with a sprinkling of sugar on top. Ideal for a summery dessert or a delightful treat any time of year.
Ingredients
Cookie Dough
- 1 cup Unsalted Butter (softened)
- 1 cup Granulated Sugar
- 1 large Egg
- 1 teaspoon Vanilla Extract
- 2 cups All-Purpose Flour
- 1 teaspoon Baking Soda
- 1/2 teaspoon Salt
Topping
- 10–12 rings Canned Pineapple (well-drained and patted dry)
- Additional Sugar (for sprinkling, to taste)
Instructions
- Preheat Oven: Preheat your oven to 350°F (180°C) to ensure it is at the correct temperature for baking the cookies evenly.
- Prepare Baking Tray: Line baking trays with parchment paper to prevent the cookies from sticking and to allow for easy cleanup.
- Cream Butter and Sugar: In a large mixing bowl, cream together the softened unsalted butter and granulated sugar using a mixer or hand whisk until the mixture is light and fluffy, about 2-3 minutes. This step is key for a soft texture.
- Add Egg and Vanilla: Beat in the large egg and vanilla extract until well combined to add moisture and flavor to the dough.
- Mix Dry Ingredients: In a separate bowl, whisk together the all-purpose flour, baking soda, and salt. Gradually add this mixture to the wet ingredients, stirring until just combined to form the cookie dough.
- Portion Dough: Scoop about 2 tablespoons of cookie dough onto the prepared baking trays, spacing each mound roughly 2 inches apart to allow room for spreading.
- Top with Pineapple: Gently press one pineapple ring onto each mound of cookie dough, slightly flattening the dough while securing the pineapple in place.
- Sprinkle Sugar: Lightly sprinkle granulated sugar over the pineapple rings to enhance caramelization and add extra sweetness.
- Bake Cookies: Place the trays in the preheated oven and bake for 11 to 13 minutes, or until the edges of the cookies are golden brown and the centers remain soft and gooey.
- Cool Cookies: Remove the cookies from the oven and allow them to cool on the baking tray for a few minutes before transferring them to a wire rack to cool completely, which helps them set and prevents sogginess.
Notes
- Ensure pineapple rings are well-drained and patted dry to prevent excess moisture from making the cookies soggy.
- You can adjust the amount of sugar sprinkled on top depending on your sweetness preference.
- For a crispier cookie, bake an additional 1-2 minutes but be careful not to overbake.
- Store cooled cookies in an airtight container at room temperature for up to 4 days.
- If using fresh pineapple rings, reduce moisture by lightly patting them dry before pressing into dough.
