Equipment You’ll Need

To make pineapple upside-down sugar cookies a success, having the right tools is just as important as using the right ingredients. This recipe is beginner-friendly, and all necessary equipment is likely already in your kitchen.

• Muffin tin
  A standard 12-cup muffin tin gives each cookie its shape and helps create the upside-down effect. For even easier release, consider using a non-stick or silicone muffin pan.

• Mixing bowls
  At least two medium to large bowls—one for mixing the dry ingredients and one for the wet.

• Electric hand mixer or stand mixer
  Creaming butter and sugar by hand is possible, but using a mixer ensures a fluffy, smooth dough.

• Measuring cups and spoons
  Precision is key when baking, especially with leavening agents and sugar ratios.

• Spatula and cookie scoop
  A spatula for scraping the bowl clean, and a cookie scoop or tablespoon for evenly portioning the dough.

• Cooling rack
  After baking and flipping, the cookies need to cool on a wire rack to maintain texture.

Using the proper equipment helps avoid sticking, uneven baking, or collapsed tops. If you’re looking for more tools to perfect your cookie game, explore make-ahead cookie recipes and tools to elevate your baking process.

Step-by-Step Instructions

Making these easy pineapple upside-down sugar cookies from scratch is simple, even for beginner bakers. Here’s a breakdown of the process:

• Preheat your oven to 350°F (175°C). Lightly grease a standard 12-cup muffin tin or line it with silicone muffin cups.

• Create the topping:

  • Pour about 1 teaspoon of melted butter into the bottom of each muffin cup.

  • Add 1 teaspoon of packed brown sugar on top and mix slightly with a spoon.

  • Place a pineapple ring in each cup. If the ring is too large, cut it to fit.

  • Add a maraschino cherry in the center of each ring.

• Prepare the dry ingredients:

  • In a mixing bowl, whisk together 2¾ cups of flour, 1 tsp baking soda, and ½ tsp baking powder. Set aside.

• Make the cookie dough:

  • In another bowl, beat 1 cup of softened unsalted butter with 1½ cups granulated sugar until light and fluffy.

  • Add 1 egg and 1 tsp vanilla extract, and mix until smooth.

  • Gradually add in the dry ingredients to form a soft dough.

• Assemble the cookies:

  • Scoop about 2 tablespoons of dough, flatten slightly, and place over each pineapple ring.

  • Gently press to cover the fruit but don’t pack tightly.

• Bake for 18–22 minutes, or until the cookie tops are lightly golden and set.

• Cool and flip:

  • Let the cookies rest in the pan for 5 minutes, then carefully invert onto a wire rack or tray while still warm to release the topping.

Expert Tips for Best Results

Mastering pineapple upside-down sugar cookies comes down to a few essential techniques that make a big difference in outcome:

• Use silicone muffin liners or a non-stick muffin tin to prevent sticking and simplify flipping.

• Drain the pineapple rings well before using to avoid soggy cookies.

• Don’t overfill the muffin cups; keep the butter and sugar layer balanced to avoid overflow.

• Slightly underbake the cookies if you prefer soft, chewy texture. They will continue cooking from residual heat once removed.

• Flip while still warm—waiting too long can cause the topping to harden and stick.

For more helpful cookie tips and visual inspiration, explore summer cookie ideas that focus on warm-weather flavors and easy prep.

Variations & Customization Ideas

One of the best parts about this recipe is how easy it is to customize. Here are some creative twists to make it your own:

• Mini pineapple chunks
  Instead of full rings, use chopped pineapple for bite-sized bursts of flavor.

• Add shredded coconut
  Mix into the dough or sprinkle on top before baking for a tropical spin.

• Spiced version
  Add ½ teaspoon of cinnamon or ginger to the brown sugar topping for warmth.

• Vegan-friendly option
  Use plant-based butter and an egg substitute like flaxseed meal or applesauce.

• Gluten-free adaptation
  Substitute all-purpose flour with a 1:1 gluten-free baking mix. Be sure to check the texture before baking.

Common Mistakes to Avoid

Even with an easy recipe, there are a few pitfalls to watch for. Avoiding these common errors will help you achieve bakery-quality results every time.

• Using overly juicy pineapple
  Failing to drain or pat dry pineapple can lead to excess moisture and soggy cookies.

• Skipping non-stick spray or liners
  Without proper greasing, the caramelized topping can stick, ruining the presentation.

• Overbaking the dough
  These cookies are best with slightly soft centers. Watch for light golden edges—not dark brown tops.

• Not flipping in time
  If cookies cool too much in the pan, the topping hardens and may stick.

• Overstuffing the muffin cups
  Keep each layer moderate to avoid overflow and uneven baking.

How to Store & Reheat

Storing these cookies correctly helps maintain their flavor and structure. Here’s how to get the most out of your batch:

• Room temperature:
  Store in an airtight container for up to 2 days.

• Refrigeration:
  Keeps them fresh for up to 5 days. Just allow them to come to room temperature before serving, or gently reheat.

• Freezing:
  These cookies freeze well. Freeze individually wrapped cookies, then store in a zip-top bag. To reheat, warm in a toaster oven or microwave for 10–15 seconds.

• Avoid stacking without parchment:
  The caramelized topping can stick, so use wax or parchment paper between layers.

For more on cookie storage techniques and best practices, view cookie storage tips that prevent sogginess and stale edges.

Serving Suggestions

Serve these pineapple upside-down sugar cookies warm or at room temperature for a crowd-pleasing dessert. They pair beautifully with:

• Vanilla ice cream for a pineapple sundae twist.

• Fresh whipped cream or toasted coconut flakes for added texture.

• Brunch boards or dessert trays as a centerpiece.

• A refreshing beverage like iced tea or a tropical cocktail.

For more presentation ideas, check out mini pineapple desserts that show creative ways to plate and decorate your cookies.

FAQs

Can I use store-bought sugar cookie dough for pineapple upside-down cookies?
Yes, you can use pre-made dough, but the flavor won’t be as rich as homemade. If using store-bought, reduce baking time slightly and monitor closely.

Can I make pineapple upside-down cookies ahead of time?
Absolutely. Bake a day in advance and store in an airtight container. Reheat slightly to re-caramelize the top before serving.

How do I keep the cookies from sticking to the pan?
Use non-stick spray or silicone muffin cups, and don’t skip the butter and sugar base.

Do I need to use maraschino cherries?
No, but they add traditional flavor and visual appeal. Alternatives include dried cranberries or diced strawberries.

Can I use crushed pineapple instead of rings?
Yes, but use in moderation to avoid excess liquid. Pat dry thoroughly and layer thinly.

Easy Pineapple Upside Down Sugar Cookies Recipe

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• Author: The Coozy Plate

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Description

These pineapple upside-down sugar cookies combine the soft, buttery texture of a classic sugar cookie with a caramelized topping of pineapple and maraschino cherry. Baked in a muffin tin and flipped warm, each cookie delivers gooey tropical flavor and vintage charm in a perfect handheld dessert. Made entirely from scratch, they’re ideal for summer gatherings, holiday tables, or casual baking days.

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Ingredients

Scale 1x2x3x

For the topping:

⅓ cup unsalted butter, melted

½ cup packed brown sugar

12 pineapple rings (canned or fresh)

12 maraschino cherries

For the sugar cookie dough:

2 ¾ cups all-purpose flour

1 tsp baking soda

½ tsp baking powder

1 cup unsalted butter, softened

1 ½ cups granulated sugar

1 egg

1 tsp vanilla extract

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Instructions

Preheat oven to 350°F (175°C). Line a muffin tin with non-stick spray or use silicone muffin cups.

 

Pour about 1 teaspoon of melted butter into the bottom of each muffin cup, followed by 1 teaspoon of brown sugar. Mix lightly with a spoon.

 

Place a pineapple ring in each cup. If needed, cut the ring to fit. Add a maraschino cherry to the center.

 

In a bowl, mix flour, baking soda, and baking powder. Set aside.

 

In another bowl, cream together the softened butter and granulated sugar until light and fluffy. Add egg and vanilla extract and beat until combined.

 

Gradually mix in the dry ingredients until a soft cookie dough forms.

 

Scoop about 2 tablespoons of dough and flatten it slightly with your hands. Place over the pineapple in each muffin cup and gently press to cover.

 

Bake for 18–22 minutes, or until the cookie tops are lightly golden.

 

Let cool for 5 minutes in the pan, then carefully invert onto a wire rack or tray while still warm so the topping comes out neatly.

 

Serve warm or at room temperature. Enjoy the gooey caramelized pineapple goodness!

Notes

• Use silicone muffin cups for the easiest release.

• Drain pineapple well to prevent soggy bottoms.

• Add a pinch of cinnamon for an extra layer of flavor in the topping.

• Freeze after baking if storing long-term. Thaw and reheat before serving.

• Try coconut flakes or nuts for texture variation.

• Flip the cookies while still warm to prevent sticking.