Pineapple Upside Down Sugar Cookies

Pineapple Upside Down Sugar Cookies on a plate with colorful garnishes

As I stood in my kitchen, the sweet scent of buttery sugar and juicy pineapple began to dance through the air, wrapping me in a cozy embrace. Memories of baking with my grandmother flooded back, each moment steeped in warmth and laughter. She had a gift for turning ordinary days into delightful culinary adventures, and her pineapple upside down cake was always a showstopper. Inspired by this nostalgia, I decided to create a twist on her classic recipe, transforming it into Pineapple Upside Down Sugar Cookies that would surely bring joy to anyone lucky enough to taste them.

These cookies are soft, chewy, and bursting with sweet-and-tart pineapple flavor, all while maintaining the iconic upside-down cake vibe we love. Pair them with a warm cup of tea or coffee, and you’ll find yourself enchanted with each succulent bite. Let’s dive into this recipe and recreate the magic together!

Recipe Timing

  • Prep Duration: 15 minutes
  • Active Cooking: 10-12 minutes
  • Total Duration: 30 minutes
  • Portion Size: About 24 cookies
  • Complexity: Simple

Nutritional Recipe

  • Calories per portion: 130
  • Protein: 1g
  • Carbs: 20g
  • Fats: 5g
  • Fiber: 0.2g
  • Sugars: 9g
  • Sodium: 40mg

Why You’ll Love This Pineapple Upside Down Sugar Cookies

What’s not to love about these delightful treats? First off, they’re incredibly easy to whip up. They bring together the classic flavors of pineapple upside-down cake with the comforting, familiar texture of a cookie. Imagine a cookie that takes you straight to the tropics with each bite — luscious pineapple bits nestled in a soft, slightly chewy base, all topped with a pop of cherry goodness. Plus, they make for a stunning presentation, perfect for any gathering or simply as a satisfying treat at home!

The Complete Cooking Journey

Now, let’s embark on this flavorful journey together. Prepping the ingredients may take just a few minutes, but the joy of baking these cookies will linger far longer. You’ll be greeted by the inviting aroma of baked goodies wafting through your kitchen, leaving you and your loved ones craving that first bite.

Ingredients:

  • 1 cup sugar
  • 1/2 cup butter, softened
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 1 1/2 cups all-purpose flour
  • 1 teaspoon baking powder
  • 1/4 teaspoon salt
  • 1 cup crushed pineapple, drained
  • Maraschino cherries (optional for garnish)

Method:

Step 1: Preheat Your Oven

Preheat the oven to 350°F (175°C). Grease a baking sheet to ensure your cookies come off easily once baked.

Step 2: Cream Sugar and Butter

In a bowl, cream together the sugar and softened butter until smooth and fluffy. This step is crucial as it creates the base for your cookies and adds a richness that’s hard to replicate.

Step 3: Incorporate Egg and Vanilla

Beat in the large egg and vanilla extract, blending until everything is well combined. The vanilla will infuse your cookies with an aromatic warmth that complements the pineapple perfectly.

Step 4: Whisk Dry Ingredients

In another bowl, whisk together the all-purpose flour, baking powder, and salt. This step ensures that your leavening agent is evenly distributed, allowing your cookies to rise beautifully.

Step 5: Combine Wet and Dry Mixtures

Gradually add the dry ingredients to the wet mixture, blending until just combined. Avoid over-mixing to keep your cookies soft and enjoyable.

Step 6: Fold in Crushed Pineapple

Gently fold in the crushed pineapple, making sure the fruit is evenly distributed throughout the dough. The pineapple will add a juicy burst of flavor, brightening each bite.

Step 7: Spoon Dough onto Baking Sheet

Using a spoon, drop generous spoonfuls of the dough onto the prepared baking sheet. Ensure there’s enough space between each mound, as the cookies will expand while baking.

Step 8: Garnish with Cherries

If desired, place a maraschino cherry on top of each cookie for a pop of color and sweetness. This touch takes the flavor and presentation over the top.

Step 9: Bake to Perfection

Bake for 10-12 minutes, or until the edges are lightly golden. Your kitchen will soon be filled with the tantalizing aroma of buttery pineapple goodness.

Step 10: Cool and Serve

Allow the cookies to cool on a wire rack before serving. This will help them firm up slightly, making them easier to handle.

Serving Suggestions & Pairings

These cookies shine on their own but can also be beautifully paired with a scoop of vanilla ice cream or a dollop of whipped cream for an elevated dessert experience. Serve them at parties, potlucks, or simply during a cozy afternoon at home.

Storage & Leftovers Guide

Store leftover cookies in an airtight container at room temperature for up to 5 days. If you want to prolong their life, stick them in the refrigerator for up to a week, or freeze them for up to three months. Just be sure to layer them with parchment paper to avoid sticking!

Kitchen Wisdom & Success Tips

  • Make it a family affair. Involve your kids in the preparation. They can help with adding the pineapple or even decorating the cookies with cherries.
  • Pineapple options. If you can’t find crushed pineapple, you can use diced fresh pineapple. Just make sure to drain it well to avoid soggy cookies.
  • Experiment! Replace the maraschino cherries with other dried fruits or nuts to create a flavor profile that suits your tastes.

Flavor Variations & Adaptations

Feel free to switch things up! You could add shredded coconut for a tropical flair, or mix in some chopped pecans or walnuts for a crunchy texture. Chocolate chips could even be a fun addition for a unique twist!

Reader Questions & Solutions

  1. What do I do if my dough is too sticky?

    • If your dough feels excessively sticky, add a little more flour, a tablespoon at a time, until it’s manageable.
  2. Can I use fresh pineapple?

    • Absolutely! Just make sure to finely chop and drain the fresh pineapple well.
  3. What if I don’t have maraschino cherries?

    • You can omit them or replace them with another small fruit like dried cranberries or blueberries.
  4. How can I make these cookies gluten-free?

    • Substitute the all-purpose flour with a gluten-free flour blend. Make sure to check the blend’s packaging for recommendations.
  5. What should I do if my cookies spread too much while baking?

    • Check your butter temperature — it should be softened, not melted. Also, try chilling the dough for 30 minutes before baking.

Wrapping Up

As you take that first bite of your Pineapple Upside Down Sugar Cookies, I hope you are transported back to simpler times filled with sweet memories. This recipe is more than just a cookie; it’s a celebration of flavors and a connection to those we love. So, gather your ingredients, embrace the joy of baking, and share these treats with friends and family. Enjoy the process — you’re creating something special, one cookie at a time!

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Pineapple Upside Down Sugar Cookies


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  • Author: camellia
  • Total Time: 30 minutes
  • Yield: 24 cookies 1x
  • Diet: Vegetarian

Description

Deliciously soft and chewy cookies bursting with sweet-and-tart pineapple flavor, inspired by the classic pineapple upside down cake.


Ingredients

Scale
  • 1 cup sugar
  • 1/2 cup butter, softened
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 1 1/2 cups all-purpose flour
  • 1 teaspoon baking powder
  • 1/4 teaspoon salt
  • 1 cup crushed pineapple, drained
  • Maraschino cherries (optional for garnish)

Instructions

  1. Preheat the oven to 350°F (175°C). Grease a baking sheet.
  2. Cream together the sugar and softened butter until smooth and fluffy.
  3. Beat in the egg and vanilla extract until well combined.
  4. In another bowl, whisk together the all-purpose flour, baking powder, and salt.
  5. Gradually add the dry ingredients to the wet mixture, blending until just combined.
  6. Fold in the crushed pineapple evenly throughout the dough.
  7. Drop generous spoonfuls of dough onto the prepared baking sheet, spacing them out.
  8. If desired, place a maraschino cherry on top of each cookie.
  9. Bake for 10-12 minutes until edges are lightly golden.
  10. Allow cookies to cool on a wire rack before serving.

Notes

Store leftover cookies in an airtight container at room temperature for up to 5 days. For prolonged storage, refrigerate for up to a week or freeze for up to three months.

  • Prep Time: 15 minutes
  • Cook Time: 12 minutes
  • Category: Dessert
  • Method: Baking
  • Cuisine: American

Nutrition

  • Serving Size: 1 cookie
  • Calories: 130
  • Sugar: 9g
  • Sodium: 40mg
  • Fat: 5g
  • Saturated Fat: 3g
  • Unsaturated Fat: 2g
  • Trans Fat: 0g
  • Carbohydrates: 20g
  • Fiber: 0.2g
  • Protein: 1g
  • Cholesterol: 30mg

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