Name: Pineapple Upside Down Cookies Recipe
Prep time: 12 min
Cook time: 10 min
Total time: 22 min
Cuisine: American
Ingredients: ½ cup Butter, softened; ½ cup Granulated Sugar (100g); 1 Large Egg; 1 teaspoon Vanilla Extract; ½ cup Powdered Sugar (65g); ¼ cup Vegetable Oil; ½ teaspoon Baking Soda; ½ teaspoon Cream of Tartar; 2 cups All Purpose Flour (240g); Pineapple Rings, drained; Maraschino Cherries, drained; 6 tablespoons Butter, melted; 1 cup Brown Sugar (214g)

Jump to Recipe· 4.4 from 59 reviews

If you’re looking for a fun twist on a classic dessert, this Pineapple Upside Down Cookies Recipe will totally steal your heart. Imagine that golden buttery crust embracing sweet pineapple rings and vibrant cherries nestled on top, then flipping it all over to reveal a caramelized tropical treat in cookie form. These little gems bring together soft, tender cookie dough with rich brown sugar caramel and juicy fruit in every bite. Whether for a party or an everyday indulgence, this recipe is a delightful way to enjoy the sunny flavors of pineapple in a portable, irresistible cookie.

Ingredients You'll Need

The image shows a metal tray on a white marbled surface with ten small white bowls and one egg neatly arranged. The top left bowl contains dark brown vanilla extract, next to it is a bowl with light yellow vegetable oil. To the right is a bowl filled with white all-purpose flour. Below the vanilla extract, a bowl holds white powdered sugar. In the center of the tray, a white egg sits alone. To the right of the egg, another bowl is filled with white granulated sugar. Just below the powdered sugar, a clear bowl contains white baking soda and baking powder. Below the egg, a small bowl holds bright red maraschino cherries. At the bottom left, a bowl is filled with light to medium brown sugar, while next to it is a white stick of butter wrapped in paper. The bottom right corner has a bowl filled with pale yellow pineapple rings. The arrangement is clean, with each ingredient clearly visible and separated photo taken with an iphone --ar 4:5 --v 7

This Pineapple Upside Down Cookies Recipe uses straightforward pantry staples that come together to create that perfect balance of sweet, soft, and buttery textures. Each ingredient plays a special role, whether providing richness, sweetness, or the right structure for the dough.

Butter (½ cup softened + 6 tablespoons melted): The backbone of flavor and tenderness, ensuring moist, melt-in-your-mouth cookies.
Granulated Sugar (½ cup): Helps to sweeten the dough while adding a delicate crumb texture.
Powdered Sugar (½ cup): Adds a subtle smoothness and helps the dough come together beautifully.
Egg (1 large): Binds the ingredients and creates that perfect chewy softness.
Vanilla Extract (1 teaspoon): Enhances the sweetness and adds warm aromatic notes.
Vegetable Oil (¼ cup): Keeps the cookies tender and moist without weighing them down.
Baking Soda (½ teaspoon): Provides a gentle lift to the dough, ensuring they’re light and airy.
Cream of Tartar (½ teaspoon): Balances the baking soda and adds a subtle tang that complements the caramel topping.
All-Purpose Flour (2 cups): The foundation for structure, giving cookies their classic chewiness.
Pineapple Rings (drained): The star of the show, juicy and sweet, they give these cookies their signature tropical twist.
Maraschino Cherries (drained): Adds a pop of color and a burst of sweetness at the center of each pineapple ring.
Brown Sugar (1 cup): Creates that rich, caramelized glaze under the pineapple for that irresistible upside down effect.

How to Make Pineapple Upside Down Cookies Recipe

Step 1: Prepare the Pan and Caramel Base

Start by preheating your oven to 350 degrees Fahrenheit to get things nice and warm. In a small bowl, mix 6 tablespoons of melted butter with 1 cup of brown sugar until smooth and combined. This mixture will form the luscious caramel base that your pineapple rings will rest on in each muffin cup. Remember to drain your pineapple rings well; excess juice can make the cookies soggy.

Step 2: Assemble Pineapple and Cherries

Place a tablespoon of your brown sugar and butter mixture into each well of a muffin tin. Press one drained pineapple ring on top, then nestle a maraschino cherry right in the center of the ring. Arranging the cookies with space between them in the pan allows each cookie to spread slightly without sticking, ensuring they keep their pretty shapes.

Step 3: Mix the Cookie Dough

In a larger bowl, cream together the softened butter and granulated sugar until the mixture is light, fluffy, and pale. This step is essential—it aerates the dough and sets the stage for soft cookies. Beat in the egg and vanilla extract for a few minutes to infuse richness and flavor. Next, slowly incorporate the vegetable oil and powdered sugar, mixing until the dough turns a lovely pale yellow and becomes smooth and creamy.

Step 4: Add Dry Ingredients and Shape Dough

Combine the flour, baking soda, and cream of tartar in a separate bowl. Gradually add this dry mixture into your wet ingredients, stirring gently just until everything is fully blended to maintain the dough’s tenderness. Using a size #24 cookie scoop or similar, portion out the dough and flatten it gently in your palm to about 3 inches in diameter.

Step 5: Assemble Cookies and Bake

Carefully press each flattened dough piece over the pineapple ring and cherry in the muffin pan, tucking the edges into the sides of the cup to seal everything in. These upside-down cookies will bake with the pineapple and cherry beneath, caramelizing beautifully. Place the pan in the oven and bake for 8 to 10 minutes, or until the edges turn a light golden brown and the centers no longer look glossy.

Step 6: Flip and Cool

Once baked, remove the pan from the oven and immediately invert it onto a parchment-lined cookie sheet. The cookies should release easily, revealing those stunning pineapple rings topped with cherries on a glossy caramel base. Let the cookies cool completely before serving so the caramel sets and the cookies hold their shape perfectly.

How to Serve Pineapple Upside Down Cookies Recipe

The image shows five pineapple upside-down cake rounds arranged on a silver wire cooling rack over a white marbled surface. Each round has three visible layers: a light golden-brown cake base, a ring of caramelized brown sugar topping, and a bright yellow pineapple slice with a shiny red cherry in the center. To the bottom right, there is a small white bowl filled with extra bright red cherries. A soft red cloth is partially visible underneath the cooling rack on the top side. The lighting is bright, enhancing the shiny and moist textures of the pineapples and cherries photo taken with an iphone --ar 4:5 --v 7

Garnishes

You can keep it simple and let the natural beauty of the pineapple and cherry shine, or add a dusting of powdered sugar for an elegant touch. For a tropical vibe, sprinkle some toasted coconut flakes on top right after flipping the cookies out, adding a bit of crunch and extra flavor.

Side Dishes

These cookies pair wonderfully with a scoop of vanilla ice cream or a dollop of whipped cream, creating an indulgent contrast between warm caramel and cool creaminess. A fresh fruit salad or even a cup of lightly brewed black tea or coffee also complements the sweet, buttery flavors perfectly.

Creative Ways to Present

Try arranging your Pineapple Upside Down Cookies Recipe on a large tropical-themed platter garnished with fresh mint leaves and slices of fresh pineapple for a stunning dessert table centerpiece. For parties, package individual cookies in clear treat bags tied with bright ribbons for a charming favor that guests will adore.

Make Ahead and Storage

Storing Leftovers

Leftover cookies keep beautifully in an airtight container at room temperature for up to 3 days. This short storage keeps the cookies soft and preserves the caramel's sticky goodness without drying out the dough.

Freezing

If you want to make these in advance, freeze the fully baked cookies in a single layer on a baking sheet first, then transfer to a sealed freezer-safe container or bag. They can last for up to 2 months frozen. Just thaw at room temperature when you're ready to enjoy.

Reheating

To reheat, warm the cookies gently in a 300-degree Fahrenheit oven for 5 to 7 minutes or pop them in the microwave for 15 to 20 seconds. This helps revive the caramel’s gooey texture and brings back that freshly baked warmth.

FAQs

Can I use fresh pineapple instead of canned rings?

Absolutely! Fresh pineapple slices work wonderfully, just be sure to slice them evenly and drain any excess juice to avoid soggy cookies. Freshness adds an even brighter flavor that’s delightful with the brown sugar caramel.

Is there a substitute for cream of tartar in this recipe?

If you don’t have cream of tartar on hand, you can use an equal amount of lemon juice or white vinegar to activate the baking soda. This creates the same gentle rise and tender crumb in the cookies.

Can I make these cookies gluten-free?

Yes! Simply swap the all-purpose flour for a gluten-free flour blend that’s meant for baking. Ensure the blend contains xanthan gum or add a small amount yourself to help maintain the cookie’s structure and texture.

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

Using a well-greased muffin tin along with the butter and brown sugar caramel base creates a natural non-stick surface. Letting the cookies cool slightly before flipping will also help them release more easily without breaking.

Can I double this Pineapple Upside Down Cookies Recipe?

Yes, doubling the recipe works well for larger gatherings. Just be sure to use multiple muffin tins or bake in batches to ensure even baking and caramelization. Keep an eye on baking times, as ovens may vary.

Final Thoughts

I can’t wait for you to try this Pineapple Upside Down Cookies Recipe—there’s something so joyful about the playful flip and the combination of tropical sweetness with caramel and buttery cookie dough. They’re perfect for sharing, gifting, or keeping all to yourself. Once you bake your first batch, these charming treats will become a beloved classic in your kitchen, bringing a little sunshine and delight to every bite.

Pineapple Upside Down Cookies Recipe

Ingredients You'll Need