Name: Pineapple Upside Sugar Cookies Recipe
Prep time: 10 min
Cook time: 15 min
Total time: 25 min
Cuisine: American
Ingredients: 1 roll (16.5 ounces) refrigerated sugar cookie dough; 1/3 cup brown sugar; 2 tablespoons unsalted butter, melted; 12 maraschino cherries, halved; 1/2 cup crushed pineapple, well drained

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If you’re craving a little sunshine, these Pineapple Upside Sugar Cookies are your ticket to instant tropical happiness—right from your own oven! Imagine all the gooey, buttery magic of a classic pineapple upside-down cake, wrapped up in the softest sugar cookie imaginable. With sweet-tart pineapple, bright maraschino cherries, and a quick caramelized brown sugar layer, this recipe transforms humble cookie dough into something playful, party-ready, and totally irresistible. Whether you serve them warm or pack them for a picnic, Pineapple Upside Sugar Cookies will add a burst of vibrant flavor to any dessert table.

Pineapple Upside Sugar Cookies Recipe - Recipe Image

Ingredients You’ll Need

You’ll love how this recipe keeps things simple yet spectacular. Every ingredient plays a starring role—from the juicy pineapple to the classic sugar cookie dough—coming together for a magical, melt-in-your-mouth treat. Let’s see how each one contributes to these unforgettable Pineapple Upside Sugar Cookies:

Refrigerated sugar cookie dough (1 roll, 16.5 ounces): This shortcut brings soft, chewy texture and sweet flavor, making your cookies a breeze to bake.
Brown sugar (1/3 cup): Adds that irresistibly caramelized layer reminiscent of traditional upside-down cakes, playing beautifully with the pineapple.
Unsalted butter, melted (2 tablespoons): Melts right into the brown sugar, ensuring every bite is rich and golden.
Maraschino cherries, halved (12): Provide a pop of color and an iconic nostalgic sweetness at the center of each cookie.
Crushed pineapple, well drained (1/2 cup): Delivers juicy, tangy bursts that balance the sugary dough and add a fresh tropical twist.

How to Make Pineapple Upside Sugar Cookies

Step 1: Prepare Your Pan and Preheat

Start by preheating your oven to 350°F and lightly greasing a standard 12-cup muffin tin. This ensures nothing sticks and gives each cookie its charming, cupcake-like shape. Greasing is key here since we’ll be layering sticky, sweet deliciousness at the bottom.

Step 2: Create the Brown Sugar-Butter Magic

Mix the melted butter and brown sugar together in a small bowl. Spoon about one teaspoon of this dreamy mixture into the bottom of each muffin cup. This forms an instant caramel layer that will bubble up around your fruit and cookie as they bake.

Step 3: Add the Cherries and Pineapple

Pop half a maraschino cherry into the center of each cup, then surround it with about two teaspoons of well-drained crushed pineapple. The key here is to drain the pineapple thoroughly so your cookies stay delightfully chewy rather than soggy.

Step 4: Top with Sugar Cookie Dough

Slice the sugar cookie dough into 12 equal pieces and gently flatten each one. Top your fruit layer with a flattened round of dough, tucking all that fruity goodness under a soft and buttery sugar cookie cap.

Step 5: Bake to Golden Perfection

Bake the Pineapple Upside Sugar Cookies for 12 to 15 minutes or until you see the edges turning a lovely golden color. The aroma of caramelized sugar and fruit will fill your kitchen and might just have your neighbors knocking on the door!

Step 6: Let Cool and Invert

Let the cookies cool in the pan for about 5 minutes. Then, gently run a knife around the edges to help them release, and carefully invert each cookie onto a wire rack or tray. That soft pineapple and cherry topping will now be shining on top, ready for admiring and enjoying.

How to Serve Pineapple Upside Sugar Cookies

Garnishes

The best garnish is sometimes the simplest! Try a light dusting of powdered sugar, tiny mint leaves, or an extra half cherry on top for even more color. If you’re feeling extra, a drizzle of vanilla glaze or melted white chocolate can turn them into true showstoppers.

Side Dishes

For a fun dessert platter, pair Pineapple Upside Sugar Cookies with other tropical treats like coconut macaroons or a scoop of coconut or vanilla ice cream. They also sit beautifully beside fresh fruit salad for a lighter finish to a summer meal.

Creative Ways to Present

Arrange the cookies on a pretty cake stand, stack them artistically on a platter, or tuck them into pastel cupcake liners for easy grab-and-go servings at picnics or parties. Kids love helping flip these upsides-down—so let them join the fun for whimsical dessert decorating!

Make Ahead and Storage

Storing Leftovers

Once cooled, store your Pineapple Upside Sugar Cookies in an airtight container at room temperature for up to three days. They keep their soft texture and signature tropical flavor—just layer with wax paper to prevent sticking.

Freezing

If you’d like to make a batch ahead (or sneak in a secret stash), these cookies freeze wonderfully. Simply wrap each cooled cookie individually in plastic wrap and freeze in an airtight container. Thaw at room temperature when those pineapple cravings strike.

Reheating

For the freshest taste, reheat Pineapple Upside Sugar Cookies in the microwave for about 10–15 seconds, just until the fruit topping is warm and syrupy. Or, pop them in a low oven (around 300°F) for a few minutes to revive that just-baked magic.

FAQs

Can I use fresh pineapple instead of canned?

Absolutely! If you have fresh pineapple on hand, chop it finely and drain any excess juice. The flavor will be even brighter and more tropical, but make sure it’s well-drained to avoid soggy cookies.

Do I need to use muffin tins for this recipe?

Using a muffin tin is recommended because it shapes the cookies into perfect little rounds and helps contain all the gooey, fruity topping. However, you could try using silicone muffin molds or mini tart pans for a similar effect.

Can I make Pineapple Upside Sugar Cookies gluten-free?

Yes! Just swap the refrigerated sugar cookie dough for your favorite gluten-free brand. Keep an eye on baking time, as some gluten-free doughs might brown faster or spread a bit differently.

What’s the best way to drain crushed pineapple?

Pour your pineapple into a fine mesh strainer or line a bowl with paper towels, then press out as much liquid as possible. The drier your fruit, the better your Pineapple Upside Sugar Cookies will hold their shape and texture.

Can I double this recipe for a party?

Definitely! Just double all ingredients and use two muffin tins (or bake in batches) to keep things moving smoothly—these cookies are always a crowd-pleaser at potlucks and parties.

Final Thoughts

If you love the flavors of an old-fashioned pineapple upside-down cake but crave the ease of a crowd-friendly cookie, Pineapple Upside Sugar Cookies are going to be your new go-to. A touch whimsical, and incredibly tasty, they’re sure to bring some sweet, sunny joy to any occasion. Happy baking!

Pineapple Upside Sugar Cookies Recipe

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4.7 from 5 reviews

Author: admin
Total Time: 25 minutes
Yield: 12 cookies 1x
Diet: Vegetarian

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Description

Indulge in a delightful twist on the classic pineapple upside-down cake with these Pineapple Upside Sugar Cookies. Each bite-sized treat features a sweet sugar cookie base topped with gooey brown sugar, juicy pineapple, and a maraschino cherry. Perfect for parties or a tropical dessert craving.

Ingredients

Scale

Ingredients:

1 roll (16.5 ounces) refrigerated sugar cookie dough
1/3 cup brown sugar
2 tablespoons unsalted butter, melted
12 maraschino cherries, halved
1/2 cup crushed pineapple, well drained

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Instructions

Preheat the oven: Preheat the oven to 350°F and lightly grease a standard 12-cup muffin tin.
Mix butter and sugar: In a small bowl, mix the melted butter and brown sugar.
Prepare muffin cups: Spoon about 1 teaspoon of the butter-sugar mixture into the bottom of each muffin cup.
Add cherries and pineapple: Place half a maraschino cherry in the center of each cup, then add about 2 teaspoons of crushed pineapple around the cherry.
Prepare cookie dough: Cut the sugar cookie dough into 12 equal portions and flatten each piece slightly.
Assembly: Place a flattened dough piece on top of the pineapple mixture in each cup.
Bake: Bake for 12–15 minutes, or until the cookies are golden around the edges.
Cool and invert: Let them cool in the pan for about 5 minutes, then run a knife around the edges to loosen and carefully invert the cookies onto a wire rack or tray.
Serve: Serve warm or at room temperature.