Pineapple Upside Down Sugar Cookies are the ultimate marriage of nostalgic comfort and sunny, tropical flair—bite-sized treats with buttery sugar cookie crusts cradling gooey caramel, golden pineapple, and dazzling cherries. Imagine all the delight of a classic pineapple upside down cake, but as charming handheld cookies you’ll want to share with everyone (or maybe not). These beauties are easy enough for a weeknight bake yet stunning enough for a special occasion, promising to bring a pop of color and a burst of flavor to any dessert table.

Pineapple Upside Down Sugar Cookies Recipe - Recipe Image

Ingredients You’ll Need

The magic of Pineapple Upside Down Sugar Cookies is that you only need a handful of simple ingredients, but each one shines and plays a starring role. Let’s go through what you’ll need, along with a few handy tips to make the flavors pop and the process a breeze!

Sugar cookie dough (1 roll, 16.5 oz): Using pre-made dough keeps things speedy and ensures consistent sweetness and texture in every cookie.
Pineapple slices (1 can, 20 oz): Their natural tartness and juiciness are the heart of these cookies, so pat them dry for best results.
Maraschino cherries (½ cup, halved): Bright, sweet, and cheerful, these are the crowning jewels in each bite-sized treat.
Light brown sugar (⅓ cup, packed): Classic for that caramel note, it melts with the butter to create a sticky-sweet base.
Unsalted butter (¼ cup, melted): The glue that binds the brown sugar topping and helps create the golden “upside down” effect.
Ground cinnamon (optional): Just a pinch can add warmth and depth, lovely if you want a subtle spice kick.

How to Make Pineapple Upside Down Sugar Cookies

Step 1: Prepare the Muffin Tin

Preheat your oven to 350°F (175°C) and give a standard 12-cup muffin tin a light greasing with butter or nonstick spray. Even if using nonstick pans, greasing helps the cookies invert easily once baked, so you get a perfect flip every time.

Step 2: Create the Buttery Caramel Base

In a small bowl, mix together your melted butter and light brown sugar until you get a grainy, golden paste. Spoon about one teaspoon of this mixture into the bottom of each muffin cup. This forms that dreamy, sticky caramel layer after baking.

Step 3: Layer the Fruit

Place one pineapple slice over the butter mixture in each cup, trimming the slices as needed so they fit comfortably. Nestle half a maraschino cherry right in the center of each pineapple ring (trust me, this makes them irresistible to look at!). If using, lightly sprinkle a pinch of cinnamon for an extra cozy touch.

Step 4: Top with Sugar Cookie Dough

Slice the sugar cookie dough into 12 even portions. Flatten each into a disc about the width of your muffin cups, then gently lay one atop each pineapple slice. Gently press down so that the dough meets the edge of the cup—they’ll bake into the perfect golden cookie cap.

Step 5: Bake to Perfection

Slide the tray into the oven and bake for 18 to 22 minutes, until the cookies turn a beautiful golden brown and look set. The magic happens here: sugar cookie dough turns crisp and the brown sugar caramelizes beneath the fruit.

Step 6: Cool and Flip

Let the cookies cool in the pan for at least 5 to 10 minutes. Then, run a knife around the edges to loosen. Carefully invert the cookies onto a wire rack or tray to reveal that glistening, fruity upside down finish. Serve them warm for gooey deliciousness, or at room temperature for chewy, caramelized bites.

How to Serve Pineapple Upside Down Sugar Cookies

Garnishes

These cookies look gorgeous right out of the pan, but you can elevate them even more! Try a fluffy dollop of whipped cream, a drizzle of caramel sauce, or a sprinkle of toasted coconut for a little extra flair—it’s both pretty and delicious.

Side Dishes

Want to build a memorable dessert platter? Pair Pineapple Upside Down Sugar Cookies with a scoop of vanilla or coconut ice cream, or even a fresh fruit salad with mango and strawberries. Their fruity tang balances rich flavors perfectly.

Creative Ways to Present

For parties, cluster the cookies on a bright serving tray and garnish with fresh mint leaves for a tropical vibe. Or stack them cupcake-style in pretty liners for easy grab-and-go treats—kids and adults alike won’t be able to resist their charm!

Make Ahead and Storage

Storing Leftovers

Once cooled, store any leftover Pineapple Upside Down Sugar Cookies in an airtight container at room temperature. They stay soft and moist for up to two days, but be aware the fruit topping will be freshest on day one.

Freezing

If you want to save some for later, freeze the fully cooled cookies on a baking sheet until solid, then transfer to a zip-top bag or airtight container. They’ll keep beautifully for up to three months without losing their vibrant flavor.

Reheating

To enjoy them warm, simply pop a cookie in the microwave for 10–15 seconds straight from the fridge (or longer from frozen). You’ll get all the gooey caramel and fruity aroma, just like fresh-baked!

FAQs

Can I use homemade sugar cookie dough instead of store-bought?

Absolutely! Homemade dough works just as well. Just make sure it holds its shape during baking and isn’t too sticky, so your Pineapple Upside Down Sugar Cookies will flip out easily and hold that perfect “upside down” look.

What’s the best way to keep the fruit from making the cookies soggy?

The secret is to drain and pat the pineapple slices and cherries very well before layering them in the muffin tin. Removing excess moisture is key to getting that perfect caramelized finish without extra sogginess.

Can I make these in advance for a party?

Yes! These cookies are delicious the day they’re baked but can be made a day ahead and stored airtight. For the absolute best texture, give them a quick warm-up just before serving to refresh the flavors and caramel topping.

Are there other fruits I could try instead of pineapple and cherries?

Sure thing! While Pineapple Upside Down Sugar Cookies are classic, you could swap in sliced peaches, pears, or even mango for a fun twist. Tiny blueberries or raspberries make a great colorful “center” alternative to cherries, too.

Can I make these gluten-free?

Of course—gluten-free sugar cookie dough (store-bought or homemade) works perfectly. Make sure to check all other ingredient labels, and you’ll still get that soft, fruity, ultra-caramelized cookie everyone will love.

Final Thoughts

There’s just something magical about Pineapple Upside Down Sugar Cookies—sweet nostalgia, tropical brightness, and pure sweetness all rolled into one easy, shareable treat. Whether you’re baking for a crowd or treating yourself to a special afternoon snack, this recipe is a showstopping favorite that never fails to impress. I hope you’ll give these a try and share them with those you love!

Pineapple Upside Down Sugar Cookies Recipe

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4.7 from 22 reviews

Author: admin
Total Time: 35 minutes
Yield: 12 cookies 1x
Diet: Vegetarian

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Description

These delightful Pineapple Upside Down Sugar Cookies are a fun twist on the classic cake version. Made with simple ingredients like sugar cookie dough, pineapple slices, and maraschino cherries, these mini treats are perfect for any occasion.

Ingredients

Scale

Sugar Cookie Dough:

1 roll (16.5 oz) refrigerated sugar cookie dough

Pineapple Layer:

1 can (20 oz) pineapple slices in juice, drained and patted dry
½ cup maraschino cherries (halved)
⅓ cup packed light brown sugar
¼ cup unsalted butter, melted
Optional: a pinch of ground cinnamon

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Instructions

Preheat and Prepare: Preheat the oven to 350°F (175°C) and grease a 12-cup muffin tin.
Mix Butter and Sugar: Combine melted butter and brown sugar, then place a teaspoon of the mixture in each cup.
Assemble: Put a pineapple slice in each cup, add half a cherry, trim if needed, sprinkle with cinnamon.
Add Dough: Divide and flatten the cookie dough, place a disc on top of each cup.
Bake: Bake for 18–22 minutes until golden, let cool for 5–10 minutes.
Invert and Serve: Run a knife around edges, invert cookies onto a rack, and serve warm or at room temperature.