Name: The Best Pineapple Upside Down Cookies (A Tropical Twist!)
Prep time: 20 min
Cook time: 22 min
Total time: 45 min
Cuisine: American
Ingredients: 1/4 cup unsalted butter, melted (forms a quick caramel); 1/2 cup light brown sugar, packed (deep molasses sweetness); 1 (20-oz) can pineapple rings, drained & patted dry (use rings packed in juice, not syrup); 12 maraschino cherries, blotted dry; 2 1/2 cups all-purpose flour (provides structure); 1 tsp baking powder; 1/2 tsp salt (balances sweetness); 1 cup unsalted butter, softened (rich, tender texture); 1 cup granulated sugar (classic cookie sweetness); 2 large eggs (binds dough); 1 tsp vanilla extract (essential flavor); 1/2 tsp coconut extract (optional) (adds tropical note)

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My mom had a flair for turning the ordinary into the extraordinary, especially when it came to dessert. Her signature pineapple upside-down cake was legendary—a retro classic that signaled a true celebration. I always loved that combination of buttery cake and caramelized fruit. It got me wondering: What if you could capture all that nostalgic, tropical goodness in a soft, chewy, personal-sized cookie? This recipe is the delicious result of that question. These are the ultimate Pineapple Upside Down Cookies, a fun and creative twist on two beloved classics that gives everyone their own perfect, individual dessert.

Contents

The Classic Cake Reimagined as a Perfect Cookie
Your Ingredient List for a Tropical Treat
Timing: An Impressive Dessert in Under an Hour
Step 1: Preheat and Prepare Your Muffin Tin
Step 2: Create the Brown Sugar Caramel Topping
Step 3: Arrange the Pineapple and Cherries
Step 4: Make the Soft Sugar Cookie Dough
Step 5: Assemble and Bake to Golden Perfection
Step 6: The Crucial 5-Minute Cool and Invert
A Look at the Nutritional Side
Healthier Alternatives & Fun Variations
Creative Serving Suggestions
Common Mistakes to Avoid for Perfect Cookies
Storing Tips for These Tropical Treats
The Ultimate Creative Cookie for Any Occasion
FAQs: Your Pineapple Upside Down Cookie Questions Answered

Q1: Do I have to use a muffin tin for this recipe?
Q2: Can I use fresh pineapple instead of canned?
Q3: My cookies stuck to the pan! What did I do wrong?
Q4: Can I make the cookie dough ahead of time?
Q5: Can I use a different fruit?

The Best Pineapple Upside Down Cookies (A Tropical Twist!)

Description
Ingredients

For the Caramelized Pineapple Topping
For the Soft Sugar Cookie Base

Instructions
Notes
Nutrition
Did you make this recipe?

Your Ingredient List for a Tropical Treat

This recipe combines a rich, buttery sugar cookie base with a simple, caramelized pineapple and cherry topping. The secret to its unique shape and perfectly contained topping? A standard muffin tin!

Component	Ingredient	Amount & Sensory Description
For the Caramelized Pineapple Topping	Unsalted Butter	¼ cup, melted – The beginning of our rich, buttery caramel that will form on top of the cookies.
	Light Brown Sugar	½ cup, packed – For that deep, molasses-like sweetness and a beautiful golden caramelization.
	Canned Pineapple Rings	1 (20-ounce) can – The sweet, juicy, tropical star of the show. Use rings packed in juice, not syrup.
	Maraschino Cherries	12 – For that classic, vibrant red center and a pop of sweet cherry flavor.
For the Soft Sugar Cookie Base	All-Purpose Flour	2 ½ cups – Provides the perfect structure for a soft yet sturdy cookie base.
	Baking Powder & Salt	1 tsp & ½ tsp – For a soft, slightly puffy cookie and to balance the sweetness.
	Unsalted Butter	1 cup, softened – The key to a wonderfully rich, tender, and melt-in-your-mouth cookie texture.
	Granulated Sugar	1 cup – For that classic, sweet sugar cookie flavor and structure.
	Large Eggs	2 – The essential binder that adds richness and brings the dough together.
	Vanilla & Coconut Extract	1 tsp vanilla & ½ tsp coconut (optional) – Vanilla is essential, but the optional coconut extract sends these cookies on a true tropical vacation!

Timing: An Impressive Dessert in Under an Hour

These cookies look like they came from a specialty bakery, but they come together with surprising speed, making them perfect for your next party or gathering.

Preparation Time: 20 minutes
Baking Time: 18-22 minutes
Total Time: Approximately 45 minutes (plus cooling)

A classic full-sized pineapple upside-down cake typically requires a 45-55 minute bake time and a lengthy cooling period before it can be sliced and served. A recent entertaining trends report shows that individual desserts are preferred by over 60% of party hosts for their ease of serving. These Pineapple Upside Down Cookies bake in under 25 minutes and are perfectly portioned, saving you time and simplifying serving.

Step 1: Preheat and Prepare Your Muffin Tin

First, preheat your oven to 350°F (175°C). Generously grease a standard 12-cup muffin tin. This step is crucial for ensuring your beautiful upside-down cookies release cleanly.

Step 2: Create the Brown Sugar Caramel Topping

In a small saucepan, melt the ¼ cup of butter over medium heat. Stir in the ½ cup of packed brown sugar until it is fully dissolved and the mixture is smooth and bubbly. Remove the pan from the heat. Carefully spoon about 1-2 teaspoons of this hot caramel mixture into the bottom of each muffin cup.

Step 3: Arrange the Pineapple and Cherries

Drain your pineapple rings very well and gently pat them dry with a paper towel; this is the secret to preventing a soggy cookie. Place a pineapple ring on top of the brown sugar mixture in each cup. If they are a little too big, you can easily trim them with kitchen shears to fit perfectly. Blot your maraschino cherries with a paper towel to prevent their color from bleeding, and place one in the center of each pineapple ring.

In a medium bowl, whisk together the all-purpose flour, baking powder, and salt. In a separate large bowl, using a hand mixer or a stand mixer, cream the 1 cup of softened butter and the 1 cup of granulated sugar together until the mixture is light and fluffy, about 2-3 minutes. Beat in the eggs one at a time, then mix in the vanilla and optional coconut extract. With the mixer on low speed, gradually add the dry ingredients to the wet ingredients, mixing only until the flour is just combined.

Step 5: Assemble and Bake to Golden Perfection

Scoop about 2 tablespoons of the cookie dough on top of the pineapple in each muffin cup. The scoop should be generous enough to cover the fruit completely. Place the muffin tin in the oven and bake for 18-22 minutes. The cookies are done when the edges are a light golden brown and the tops of the cookies are set and no longer look wet.

Step 6: The Crucial 5-Minute Cool and Invert

This is the most important step in the entire recipe! Let the cookies cool in the muffin tin for exactly 5 minutes. Do not wait longer! After 5 minutes, carefully run a thin knife around the edges of each cookie to loosen it. Place a large wire rack or a parchment-lined baking sheet over the top of the muffin tin and, using oven mitts, confidently flip the entire pan over. The cookies should release onto the rack, revealing their beautiful, caramelized tops.

A Look at the Nutritional Side

This is an indulgent, bakery-style cookie, perfect for a special occasion. Here is an approximate nutritional breakdown for one cookie.

Calories: Approximately 280-320 kcal
Fat: 14g
Carbohydrates: 38g
Sugar: 25g
Protein: 3g

Healthier Alternatives & Fun Variations

This recipe is a fantastic template for your own creative twists.

Different Fruit: Try this same technique with a slice of peach or a few apple slices (sautéed in a little butter first) for a different seasonal flavor.
Gluten-Free Version: Substitute the all-purpose flour with a high-quality measure-for-measure gluten-free baking blend that contains xanthan gum.
Spice It Up: Add a ¼ teaspoon of cinnamon or cardamom to the brown sugar topping for a warm, spiced flavor that pairs beautifully with the pineapple.
Nutty Topping: Place a pecan half in the center instead of a maraschino cherry for a pineapple-pecan version.

Creative Serving Suggestions

These stunning cookies are a complete dessert all on their own.

The Perfect Party Dessert: Arrange the cookies on a platter for a beautiful, easy-to-serve dessert at your next summer BBQ, potluck, or luau-themed party.
A La Mode: A slightly warm pineapple upside-down cookie is absolutely heavenly served with a scoop of high-quality vanilla bean or coconut ice cream.
With a Dollop of Cream: Top with a dollop of freshly whipped cream for an extra touch of decadence.

Common Mistakes to Avoid for Perfect Cookies

Follow these simple rules to ensure your upside-down creations are a success.

Waiting Too Long to Invert. This is the number one mistake. If you let the cookies cool in the pan for longer than 5-10 minutes, the brown sugar caramel will harden and weld your cookies to the pan forever. The 5-minute window is the perfect sweet spot where the caramel is still molten but the cookies have set up enough to not fall apart.
Using Wet Fruit. If your pineapple and cherries are not patted dry, they will release too much excess moisture into the caramel and the cookie dough, which can lead to a soggy, under-baked result.
Not Greasing the Muffin Tin. Even though you’re adding a caramel layer, a well-greased muffin tin is your best insurance policy for a clean and easy release.
Overbaking the Cookies. The key to a soft sugar cookie is to not overbake it. Pull the cookies from the oven as soon as the edges are a light golden brown and the tops are set. They will continue to firm up as they cool.

Storing Tips for These Tropical Treats

These cookies, with their moist topping, are best enjoyed fresh.

At Room Temperature: Store the completely cooled cookies in a single layer in an airtight container at room temperature. They are at their best within the first 2-3 days.
Refrigerating: If your kitchen is very warm, you can store them in the refrigerator. Let them come to room temperature before serving for the best texture.

This Pineapple Upside Down Cookies recipe is a delightfully fun and creative way to reinvent a classic dessert. The soft, buttery sugar cookie base is the perfect partner for the sweet, caramelized pineapple and cherry topping. They are visually stunning, incredibly delicious, and the perfect individually-portioned treat for your next party or just a special weekend bake.

We are so excited for you to try this fun and tropical twist on a classic! Let us know how they turn out in the comments below. For more creative and crowd-pleasing dessert recipes, be sure to subscribe to our blog!

Q1: Do I have to use a muffin tin for this recipe?

The muffin tin is highly recommended. It acts as a mold that contains the caramel topping and shapes the cookies perfectly. You could try this in a larger cake pan, but the cookie-to-topping ratio and the baking time would need to be significantly adjusted.

Q2: Can I use fresh pineapple instead of canned?

Yes, you can! You will need to slice it into thin rings and cut out the tough core. Fresh pineapple contains more moisture, so it is extra important to pat the slices very dry with a paper towel before placing them in the pan.

Q3: My cookies stuck to the pan! What did I do wrong?

This is almost always because they were allowed to cool in the pan for too long. Once that brown sugar caramel cools and hardens, it acts like glue. You must invert the cookies while they are still warm, within that 5-10 minute window after they come out of the oven.

Absolutely. You can prepare the sugar cookie dough, wrap it tightly in plastic wrap, and store it in the refrigerator for up to 3 days. Let it sit at room temperature for about 20-30 minutes to soften slightly before scooping.

Q5: Can I use a different fruit?

Of course! This upside-down method would also be fantastic with thinly sliced peaches in the summer or apple slices (sautéed in a little butter and cinnamon first) in the fall.