Pineapple Upside Down Cookies Recipe

If you’re craving a fun twist on a classic dessert, this Pineapple Upside Down Cookies Recipe is exactly the treat you need! I absolutely love how these cookies capture all those caramelized, tropical flavors in a handheld form, perfect for sharing at your next party or family gathering. The combination of sweet pineapple rings and cherries nestled beneath soft, buttery cookies is just irresistible.

When I first tried making these, I was amazed at how easy they came together and how dramatically they impressed everyone around the table. You’ll find that this Pineapple Upside Down Cookies Recipe works wonderfully for a quick dessert craving or even as a charming gift to bring to your neighbor’s house. Plus, they bake up beautifully in just minutes, so you’re not stuck waiting forever to indulge!

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Ingredients You’ll Need

The beauty of the Pineapple Upside Down Cookies Recipe is how simple yet well-matched the ingredients are. Each one plays a crucial role in creating that classic caramelized fruit flavor with moist, tender cookie layers.

• Butter: Using softened butter for the dough gives you that rich and creamy texture; melted butter blends well with the brown sugar topping.
• Granulated Sugar: Essential for creaming with butter, this helps your cookies puff just right without being overly sweet.
• Egg: Binds everything together and adds moisture for that tender bite.
• Vanilla Extract: A splash of vanilla elevates the flavor, rounding out the sweetness with a warm note.
• Powdered Sugar: This brings a smooth sweetness to the dough and helps maintain a soft texture.
• Vegetable Oil: Adds moisture and softness without weighing down your cookies.
• Baking Soda: Helps the cookies rise and become light and airy.
• Cream of Tartar: Keeps the cookies tender by stabilizing the baking soda reaction.
• All-Purpose Flour: The base that gives your cookies structure; measuring it correctly is key for perfect texture.
• Pineapple Rings: Make sure they’re well drained — excess moisture can make your cookies soggy.
• Maraschino Cherries: Adds a pop of color and a burst of sweetness nestled in the center of the pineapple ring.
• Brown Sugar: For that delicious caramelized topping that melts into the butter perfectly.
• Butter (for topping): Melted and combined with brown sugar to create that iconic sticky, gooey layer.

Variations

One of the things I love about the Pineapple Upside Down Cookies Recipe is how easy it is to make your own with small tweaks. Feel free to switch up the fruit or add your favorite mix-ins for a cookie that’s totally your style.

• Tropical Twist: I once added diced mango alongside the pineapple for a fresh, juicy surprise that my family adored.
• Gluten-Free: Swap in a gluten-free flour blend to make these cookies safe for everyone; they still turn out super tasty!
• Vegan Version: Use vegan butter and a flax egg instead of regular egg – you won’t miss a thing in flavor or texture.
• Extra Spice: Adding a pinch of cinnamon or ginger to the dough gives the cookies a warm, cozy feel that’s perfect for cooler months.

How to Make Pineapple Upside Down Cookies Recipe

Step 1: Prepare Your Pan with the Caramelized Topping

Start by preheating your oven to 350°F — this sets the perfect temperature for even baking. In a small bowl, mix the melted butter and brown sugar until it’s smooth and shiny. This mixture is the base for your gorgeous caramelized pineapple topping. Spoon about a tablespoon of this mixture into each well of a muffin tin. Then, place one well-drained pineapple ring on top of the sugar mixture, topping it with a maraschino cherry in the center. I like to stagger the placement of the cookie dough later to give each cookie room to spread without sticking together — trust me, it makes a difference!

Step 2: Make the Cookie Dough

Cream together the softened butter and granulated sugar until fluffy and light — this takes about 2 to 3 minutes and really helps the cookies get that tender crumb. Add in the egg and vanilla extract, beating again until everything is well combined. Next, gradually blend in the vegetable oil and powdered sugar; the dough will be creamy and pale yellow. In a separate bowl, whisk together the flour, baking soda, and cream of tartar, then slowly mix this into the wet ingredients until fully incorporated. The dough will be soft but manageable.

Step 3: Shape and Bake Your Cookies

Using a cookie scoop or spoon, portion out the dough (I use a size #24 scoop) and press each ball flat with your palm to about 3 inches wide. Gently place the flattened dough on top of each pineapple ring and cherry, carefully tucking the edges into the sides of the muffin well to seal everything in. This step ensures your cookies bake around the fruit and hold their shape. Bake the cookies for 8 to 10 minutes, watching for edges to turn golden and centers to stop looking glossy.

Step 4: Flip and Cool

This is the fun part! Remove the pan from the oven and immediately flip the muffin tin onto a parchment-lined baking sheet. The cookies will gently fall out, revealing the pineapple rings and cherries on top in that classic, magical upside-down way. Allow them to cool completely before serving — this keeps the caramel topping nice and sticky without being messy.

How to Serve Pineapple Upside Down Cookies Recipe

Garnishes

I love to garnish these cookies with a little dusting of powdered sugar or a drizzle of honey for extra shine and sweetness. Fresh mint leaves also add a nice pop of color and freshness that balances the rich caramelized topping perfectly.

Side Dishes

These cookies pair amazingly with a scoop of vanilla ice cream or a dollop of whipped cream to complement their tropical sweetness. For a more grown-up pairing, a cup of chai tea or a cold glass of pineapple-infused sparkling water rounds out the experience beautifully.

Creative Ways to Present

For parties, I’ve arranged these cookies on a large tropical-themed platter surrounded by fresh pineapple chunks and maraschino cherries to tie in the theme. Wrapping individual cookies in clear cellophane tied with a bright ribbon also makes a charming edible gift that friends adore.

Make Ahead and Storage

Storing Leftovers

Store your Pineapple Upside Down Cookies in an airtight container at room temperature for up to 7 days. From my experience, they taste best within 2 to 3 days when the topping stays perfectly moist, but they remain enjoyable even after that.

Freezing

Freezing isn’t my favorite for this recipe because the pineapple and cherry release water when thawed, which can make the cookies soggy. If you do freeze, wrap each cookie tightly and eat them within a month for the best quality.

Reheating

To warm up leftover cookies, I pop them in a preheated oven at 300°F for about 5 minutes. This refreshes their softness and reactivates the caramel topping’s gooey goodness without drying them out like a microwave tends to do.

FAQs

Final Thoughts

This Pineapple Upside Down Cookies Recipe quickly became one of my favorites because it hits that perfect nostalgic note with a modern, portable twist. The sweet caramelized fruit topping baked right into a soft cookie is something everyone should experience at least once. I really hope you give this recipe a try — it’s fun to make, delightful to eat, and even better when shared with friends or family. Trust me, you’re going to get so many compliments!

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