If you have a sweet tooth and a love for nostalgic flavors, the Pineapple Upside-Down Cookies Recipe is going to become your new obsession. These charming little treats capture all the delightful elements of a classic pineapple upside-down cake but in perfectly portioned, handheld cookies. Imagine golden, buttery cookie dough wrapped around caramelized brown sugar and juicy pineapple with a cherry on top. Each bite is a burst of tropical sweetness balanced by a tender crumb and a hint of tang from the sour cream. It’s like summer and comfort food joined forces to create something truly irresistible.

Pineapple Upside-Down Cookies Recipe - Recipe Image

Ingredients You’ll Need

This Pineapple Upside-Down Cookies Recipe relies on simple, classic ingredients that are easy to find yet essential for delivering that perfect texture and flavor. Each one plays a special role in making these cookies supremely soft, sweet, and beautiful.

Unsalted butter: Melted for the topping to create that luscious caramel layer and softened for the dough to add richness and tenderness.
Light brown sugar: Used in both the topping and dough, it provides a deep, molasses-like sweetness that complements the pineapple perfectly.
Canned pineapple rings: The star ingredient, bringing juicy, tropical brightness; halved or trimmed to fit your cookie molds snugly.
Maraschino cherries: Adds a pop of color and a sweet, slightly tangy finish to each cookie’s crown.
Granulated sugar: Balances sweetness and helps create the cookie’s soft yet sturdy crumb.
Eggs: Bind the dough and contribute to its tender structure.
Vanilla extract: Enhances the overall flavor with warm, inviting notes.
Sour cream: Adds moisture and a subtle tang that keeps the cookies from being too sweet or heavy.
All-purpose flour: The base of the dough, providing structure.
Baking powder and baking soda: Leavening agents that ensure a light, fluffy texture.
Salt: Balances sweetness and intensifies the flavors.
Cornstarch: Softens the cookie’s texture for a melt-in-your-mouth feel.

How to Make Pineapple Upside-Down Cookies Recipe

Step 1: Prepare Your Oven and Muffin Pan

Start by preheating your oven to 350°F (175°C). While it’s warming up, lightly grease or spray a muffin pan to make sure those cookies come out cleanly and keep their beautiful presentation intact. This step is crucial because it sets the stage for the caramelized pineapple topping.

Step 2: Create the Topping Base

Pour about one teaspoon of melted butter and one teaspoon of brown sugar into each muffin cup. These ingredients will bubble up in the oven, turning into the caramel layer that perfectly hugs the pineapple. Be sure not to skip this step—it’s what gives these cookies their signature magic.

Step 3: Arrange Pineapple and Cherries

Next, place a halved pineapple ring in each muffin cup on top of the butter and sugar, followed by one maraschino cherry nestled in the center. This combination creates that classic Pineapple Upside-Down look and flavor, so take a moment to arrange them neatly as it really enhances the final appearance.

Step 4: Mix the Cookie Dough

In a large bowl, beat the softened butter with granulated sugar and brown sugar until fluffy and light. This mix will give your cookies a rich buttercream-like base that’s wonderfully soft. Then, add eggs one at a time, mixing thoroughly after each addition to maintain a uniform texture. Stir in the vanilla extract and sour cream next—these two ensure your cookies stay moist and tender.

Step 5: Combine Dry Ingredients and Form Dough

In another bowl, whisk together the flour, baking powder, baking soda, salt, and cornstarch. Gradually add this dry mixture into your wet ingredients, blending gently just until everything comes together to form a soft dough. Avoid overmixing here to keep your cookies from becoming tough.

Step 6: Assemble and Bake

Spoon or scoop the cookie dough over each pineapple-cherry topping, filling the muffin cups almost to the brim. This layering creates the iconic upside-down effect once baked. Place the pan in the oven and bake for 18 to 22 minutes, or until the cookies turn a golden shade and feel set around the edges but still tender inside.

Step 7: Cool and Invert

Once the timer goes off, allow your cookies to cool in the pan for about 10 minutes. This cooling time is critical to let the caramel set so that when you carefully invert the pan onto a wire rack, the pineapple-cherry topping stays perfectly intact and gloriously glossy. This moment is pure joy—you get to reveal the delightful upside-down surprise!

How to Serve Pineapple Upside-Down Cookies Recipe

Garnishes

To elevate the presentation, add a dusting of powdered sugar or a light drizzle of honey right before serving. Fresh mint leaves also make a beautiful contrast, adding a refreshing brightness that complements the sweet pineapple perfectly.

Side Dishes

These cookies pair wonderfully with a scoop of vanilla ice cream or a dollop of whipped cream for a classic combination that’s hard to resist. If you’re wanting something lighter, a cup of hot tea or coffee balances the sweetness and creates a cozy, relaxing treat.

Creative Ways to Present

Try serving the Pineapple Upside-Down Cookies Recipe on a tropical-themed platter with vibrant napkins and colorful cocktail umbrellas to really bring the island vibe to your table. You can also place each cookie in a decorative cupcake liner for easy handling if you’re sharing at a party or potluck.

Make Ahead and Storage

Storing Leftovers

Store any leftover Pineapple Upside-Down Cookies in an airtight container at room temperature for up to three days. Keeping them sealed helps maintain that soft texture and prevents them from drying out. For longer storage, refrigeration is possible but not preferred, as it can firm up the butter and affect softness.

Freezing

If you want to prepare these delightful cookies ahead of time, freeze them after they have cooled completely. Wrap each cookie individually in plastic wrap and place them in a freezer-safe bag or container. They’ll keep well for up to two months and thaw beautifully without losing texture.

Reheating

To reheat, gently warm the cookies in a low oven (around 300°F or 150°C) for 5 to 8 minutes. This brings back the fresh-baked softness and reactivates the caramel topping’s stickiness. Avoid microwaving as it can turn the cookies soggy or overly soft.

FAQs

Can I use fresh pineapple instead of canned?

Fresh pineapple can work, but canned pineapple tends to hold its shape and moisture better during baking. If you use fresh, make sure it’s well drained and sliced thinly to fit the muffin cups.

What type of pan is best for making these cookies?

A standard muffin pan is ideal because it creates perfectly sized cookies and holds the pineapple and topping in place as they bake. Avoid using silicone pans as the caramel might not set correctly.

How do I prevent the cookies from sticking when I invert them?

Lightly greasing the pan is essential. Also, make sure to let the cookies cool for about 10 minutes before flipping, so the caramel solidifies slightly, reducing stickiness and keeping the topping intact.

Can I make these cookies vegan?

You can experiment with vegan butter, plant-based sour cream, and an egg substitute, but these swaps might alter the texture and flavor somewhat. The original recipe’s richness comes from its dairy and eggs.

Why is there cornstarch in the dough?

Cornstarch helps soften the cookie’s crumb and improves the overall texture, giving these cookies their tender, almost melt-in-your-mouth quality, which is important for balancing the dense topping.

Final Thoughts

This Pineapple Upside-Down Cookies Recipe brings together the best of comfort and tropical flavors in a fun, easy-to-share form. Whether it’s for a summer gathering, a weeknight treat, or just because you deserve something sweet, these cookies deliver happiness in every bite. I can’t wait for you to try them and fall in love just like I did.