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Pineapple Upside Down Sugar Cookies: Easy Mini Recipe for Holiday Delights
Craving a delicious dessert that’s both nostalgic and surprisingly simple? You want to bake something that wows your guests but doesn’t require a full day in the kitchen, leading you to the perfect idea: Pineapple Upside Down Sugar Cookies.
Pineapple Upside Down Sugar Cookies are a delightful holiday treat made by layering a brown sugar caramel, a pineapple ring, and a maraschino cherry in a muffin tin, then topping with a soft sugar cookie dough. When baked and inverted, they create a beautiful, handheld version of the classic pineapple upside-down cake that is sweet, buttery, and juicy. This easy recipe yields perfect results every time.
Based on a time-tested method and expert baking advice, this guide ensures you achieve the perfect balance of a fluffy cookie and a perfectly caramelized topping. You will learn the secrets to preventing common issues like sogginess or sticking. Get ready to master a dessert that looks as amazing as it tastes.
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Transforming a classic cake into a portable, party-ready treat is easier than you think. This guide breaks down the entire process for making perfect Pineapple Upside Down Sugar Cookies into seven simple, foolproof stages. We will build the cookie from the bottom up, starting with the crucial preparation of the Muffin Tin and fruit, creating the rich Brown Sugar Glaze, mixing the perfect Sugar Cookie Dough, and finishing with the magical inversion that reveals the beautiful final product. Follow along to create a sunshine-filled delight that will become your new go-to recipe.
1. Prepare the Muffin Tin & Pineapple Slices
Pin this essential first step for flawless pineapple cookies!
Proper preparation is the secret to success. The muffin tin acts as the vessel that enables portion control and shapes each cookie perfectly. Most importantly, preparing the fruit correctly by removing excess moisture is the single best way to guarantee a chewy cookie, not a soggy one. This initial step sets the foundation for a flawless bake.
Supplies Needed
- 1 standard 12-cup muffin tin
- Non-stick baking spray with flour
- 1 (20 ounce) can canned pineapple rings in juice
- Paper towels
Steps
- Preheat oven to 350°F (175°C).
- Thoroughly grease the muffin tin with non-stick baking spray. Ensure you cover the bottom and sides of each cup to guarantee a clean release.
- Drain the canned pineapple rings completely.
- Press each pineapple ring gently between layers of paper towels to remove as much excess moisture as possible. This is the most important step to prevent sogginess.
Pro-Tip: For truly dry pineapple, let the drained rings sit on paper towels for 10-15 minutes before you begin. The hygroscopic properties of sugar mean the caramel will draw any available moisture, and starting with dry fruit is key to a chewy, not soggy, cookie.
2. Create the Brown Sugar Caramel Base
Save this simple caramel method for all your baking!
The signature gooey topping comes from a simple two-ingredient brown sugar glaze. Combining melted unsalted butter and packed brown sugar creates the base that will caramelize in the oven, infusing the entire cookie with a rich, buttery sweetness. This no-fuss method is quick and delivers that classic pineapple upside-down flavor.
Ingredients
- 1/2 cup (1 stick) unsalted butter, melted
- 1 cup packed light brown sugar
Instructions
- In a small bowl, mix the melted unsalted butter and packed brown sugar until fully combined. The mixture will be thick and grainy.
- Spoon approximately 1 tablespoon of the brown sugar mixture into the bottom of each prepared muffin cup.
- Press the mixture down lightly with the back of the spoon to create an even layer.
Pro-Tip: Don’t overcook the mixture on the stove. Simply melting the butter and combining it with the sugar is enough. The true caramelization stages and Maillard reaction will occur in the oven, creating a deeper flavor without the risk of burning the sugar upfront.
Your go-to soft sugar cookie recipe starts here!
The foundation of this treat is a perfectly soft, fluffy sugar cookie base. This from-scratch dough is simple to make and provides the ideal texture to complement the juicy fruit and caramel. Its flavor complements vanilla wonderfully and creates a cookie that is sturdy enough to hold the topping yet melts in your mouth. We also include a popular shortcut for when time is short.
Ingredients
- 1 1/2 cups all-purpose flour
- 1/2 teaspoon baking soda
- 1/4 teaspoon salt
- 1/2 cup (1 stick) unsalted butter, softened
- 3/4 cup granulated sugar
- 1 large egg
- 1 teaspoon vanilla extract
Instructions
- In a medium bowl, whisk together the all-purpose flour, baking soda, and salt. Set aside.
- In the bowl of a stand mixer (or using a hand mixer), beat the softened butter and granulated sugar together on medium speed until light and fluffy, about 2-3 minutes.
- Beat in the egg and vanilla extract until well combined.
- Reduce the mixer speed to low and gradually add the flour mixture, mixing only until just combined. Do not overmix.
Time-Saving Tip (Pillsbury Hack): In a hurry? This recipe works beautifully with one (16.5 oz) roll of refrigerated Pillsbury sugar cookie dough. Simply skip this “from scratch” step and proceed to assembling the cookies. This is the fastest way to get your handheld pineapple upside down cake fix!
The fun part! Pin this assembly guide for later.
Now it’s time to bring all the components together. The key to that iconic look is to layer everything in the correct order. The pineapple slice and maraschino cherry sit on the caramel, waiting to become the jeweled topping. The cookie dough is then layered on top, which covers the fruit and forms the cookie’s base once inverted.
Supplies Needed
- Assembled muffin tin with caramel base
- Drained pineapple rings
- 12 maraschino cherries, stems removed
- Prepared sugar cookie dough
Directions
- Arrange one pineapple slice in each muffin cup, on top of the brown sugar mixture.
- Place one maraschino cherry in the center of each pineapple ring.
- Scoop about 2 tablespoons of cookie dough (or a slice from the pre-made roll) and flatten it slightly in your palm.
- Layer the flattened dough disc over the pineapple and cherry, pressing down gently to seal the edges against the sides of the muffin cup. The dough should cover the fruit completely.
Pro-Tip: Use a medium cookie scoop (about 1.5 to 2 tablespoons) for uniform dough portions. This ensures every cookie bakes evenly and has the perfect cookie-to-fruit ratio.
5. Bake to Golden Brown Perfection
Don’t forget to save this baking time and temperature tip!
The magic happens in the oven. As the cookies bake, the butter and sugar on the bottom will bubble and caramelize, while the cookie dough puffs up to a perfect golden brown. Knowing the right baking time and temperature, and looking for the right visual cues, is essential for a perfectly cooked-through cookie.
Equipment Needed
- Prepared oven
- Muffin tin filled with cookie assemblies
Directions
- Place the muffin tin on the center rack of your preheated 350°F (175°C) oven.
- Bake for 18-22 minutes.
- The cookies are done when the cookie tops are a light golden brown and the edges are slightly darker and pulling away from the sides of the pan. You may see some bubbling caramel around the edges.
Pro-Tip: For even baking, rotate the muffin tin halfway through the baking time. If you’re unsure about doneness, a toothpick inserted into the cookie part (not the fruit) should come out with moist crumbs, not wet batter.
6. The Perfect Inversion Technique
The magic moment! Pin this trick for a clean release every time.
This is the most crucial and satisfying step: the reveal. The inversion process requires precise timing. Letting the cookies cool for just a few minutes allows the caramel to set slightly, but not so much that it hardens in the pan. A quick, confident flip is all it takes to avoid sticking and achieve a beautiful clean release.
Supplies Needed
- Hot muffin tin from the oven
- A large baking sheet or cooling rack lined with parchment paper
- Oven mitts
Steps
- Remove the muffin tin from the oven and place it on a heat-resistant surface.
- Let the cookies cool in the pan for exactly 5 minutes. Do not wait longer, or the caramel will harden and stick to the pan.
- Place the parchment-lined baking sheet over the top of the muffin tin.
- Wearing oven mitts, firmly grasp both the muffin tin and the baking sheet, and in one quick, confident motion, invert (flip) them.
- Lift the muffin tin away. The cookies should release onto the baking sheet.
Pro-Tip: If any pineapple or caramel topping sticks in the pan, don’t panic! Simply use a small spoon or spatula to scoop it out and place it back on top of its cookie while everything is still warm.
7. Cool and Serve Your Tropical Treats
The grand finale! Save this for your next party or cookie swap idea.
The best way to enjoy your beautiful creations is to serve warm, allowing the caramel to be soft and the cookie tender. A short cooling period lets them set up perfectly for serving. We’ll also cover the best way to store them so you can enjoy this tropical treat for days to come. The finished cookie pairs with accompaniments like vanilla ice cream beautifully.
Supplies Needed
- The finished, inverted cookies
- Optional: Vanilla ice cream or whipped cream for serving
What To Do
- Allow the cookies to cool on the parchment paper for at least 10 minutes before serving. They are delicious served warm, but this rest period allows the caramel to set slightly.
- If not serving immediately, let the cookies cool completely to room temperature before moving.
- To store, place the cookies in a single layer in an airtight container. They will stay fresh at room temperature for up to 3 days.
Pro-Tip: For an extra decadent summer treat, serve a warm cookie topped with a small scoop of high-quality vanilla ice cream. The contrast of warm, caramelized fruit and cool cream is unforgettable.
- Dry Pineapple is Non-Negotiable: The most critical step to prevent sogginess is to thoroughly drain and pat dry your pineapple slices with the paper towel method. Excess moisture is the enemy of a perfect cookie.
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The 5-Minute Inversion Rule: After baking, you must let the cookies cool for exactly 5 minutes before you invert them. This ensures the caramel is liquid enough for a clean release but not so hot that it’s runny.
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Grease the Pan Generously: To avoid sticking, use a non-stick baking spray with flour and be sure to coat the bottom and sides of every muffin tin cup. This is your insurance policy.
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From-Scratch or Shortcut Works: This tested recipe is versatile. You can make the soft sugar cookie dough from scratch for a homemade touch or use Pillsbury sugar cookie dough for a quick and easy Pillsbury hack.
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Serve Warm for the Best Experience: These cookies are at their peak when served warm, but not hot. This allows the caramelized pineapple flavor to shine and the texture to be perfectly soft and chewy.
The key to preventing soggy cookies is aggressive moisture management. Before you begin, drain your canned pineapple thoroughly, then press the rings firmly between layers of paper towels. Removing as much juice as possible ensures the cookie base bakes up soft and chewy, not wet and dense. Never use pineapple packed in heavy syrup.
Yes, absolutely! This is a fantastic shortcut. A 16.5-ounce roll of refrigerated sugar cookie dough, like Pillsbury, works perfectly. Simply slice the dough into 12 equal rounds and place one on top of each pineapple and cherry before baking. It’s the easiest way to make this impressive dessert.
Sticking usually happens for two reasons: improper greasing or cooling too long. First, ensure you’ve generously greased your muffin tin with a baking spray that contains flour. Second, you must invert the cookies after exactly 5 minutes of cooling. If you wait longer, the caramel will cool and harden, acting like glue.
Should I use fresh or canned pineapple?
For this specific recipe, canned pineapple rings are highly recommended. Canned pineapple has a more consistent sweetness and texture, and it’s already perfectly shaped. While fresh pineapple is delicious, it releases more variable amounts of juice during baking, which can lead to sogginess and make the outcome less predictable.
Bake the cookies at 350°F (175°C) for 18 to 22 minutes. You’re looking for the sugar cookie tops to be a light golden brown and for the caramel around the edges to be bubbly. Ovens can vary, so start checking at the 18-minute mark for these visual cues.
Yes, you can freeze them, but with specific steps for best results. Let the cookies cool completely. Place them on a baking sheet in a single layer and “flash freeze” for one hour. Then, wrap each cookie individually in plastic wrap and store them in an airtight freezer bag. To serve, thaw them at room temperature.
Store the completely cooled cookies in a single layer in an airtight container at room temperature. They will stay fresh for up to 3 days. Do not refrigerate them, as the cold temperature can make the cookie base hard and dry out the texture.
Can I use pineapple tidbits instead of rings?
Yes, you can use pineapple tidbits or crushed pineapple, but you must drain it exceptionally well. If using crushed pineapple, press it in a fine-mesh sieve to remove all excess juice. The final look will be different—more of a mosaic topping—but the tropical flavor will be just as delicious.
What’s the difference between this and the pineapple upside down cake?
The main difference is the base and the format. A traditional cake uses a light, airy cake batter, while this recipe uses a denser, chewier sugar cookie dough. This results in a handheld, individually portioned dessert with a satisfying cookie texture, making it easier to serve and perfect for parties.
A standard 12-cup muffin tin is essential for this recipe. The cups are crucial for containing the caramel and fruit, allowing the cookie dough to bake on top and create the signature “upside down” shape. A baking sheet will not work as the caramel would spread everywhere.
Final Thoughts on Your New Favorite Holiday Delight
You now have the complete, tested framework for creating stunning Pineapple Upside Down Sugar Cookies that taste even better than they look. By mastering a few key techniques—like properly drying the pineapple and nailing the 5-minute inversion window—you can confidently produce a dessert that brings the best of a classic cake and a beloved cookie into one perfect, handheld bite. Whether you choose the from-scratch dough or the clever Pillsbury hack, the result is a gloriously gooey, fruity, and satisfying treat.
These cookies are more than just a recipe; they’re a centerpiece for your next summer party, a welcome addition to a holiday cookie swap idea, or simply a cheerful bite of sunshine on any given day. Which occasion will you bake these for first?
Last update on 2026-02-27 at 21:49 / Affiliate links / Images from Amazon Product Advertising API
