From My Kitchen To Yours...
All Word Recipes

Pineapple Upside Sugar Cookies

If you love the sweet, tangy flavors of pineapple upside-down cake, you’ll adore these Pineapple Upside Down Sugar Cookies! These delightful cookies combine the buttery sweetness of sugar cookies with a juicy pineapple topping, all baked into a perfect, chewy bite. Topped with maraschino cherries and a hint of brown sugar, these cookies bring the tropical flavors of the beloved dessert into a fun, handheld treat.

Perfect for summer barbecues, holiday gatherings, or just as an indulgent afternoon snack, these cookies are easy to make and pack a burst of flavor in every bite. With their simple, yet elegant design, Pineapple Upside Down Sugar Cookies are sure to be a hit at any occasion.

Whether you’re making them for a special event or just treating yourself to a tropical-inspired snack, these cookies will transport you to a sunny paradise. They’re sweet, fruity, and oh-so-delicious—what’s not to love?

Pineapple Upside Down Sugar Cookies are a fun and tropical twist on the classic pineapple upside-down cake. These chewy sugar cookies are topped with sweet pineapple rings, a sprinkle of brown sugar, and a maraschino cherry, all baked into a perfect, bite-sized treat. The combination of the buttery sugar cookie base with the caramelized pineapple makes these cookies irresistible.

Remember It Later

This recipe! Pin it to your favorite board NOW!

Pin

They’re a great way to add a tropical flair to any cookie tray, and they’re perfect for any occasion that calls for something sweet and different. Whether you’re baking for a summer picnic or a festive holiday party, Pineapple Upside Down Sugar Cookies will be a crowd favorite.

Exciting Story:

I first made Pineapple Upside Down Sugar Cookies when I was looking for a way to combine two of my favorite things—sugar cookies and pineapple upside-down cake. I’ve always loved the tropical sweetness of pineapple paired with the rich, buttery goodness of a sugar cookie, and I thought, “Why not combine them into one delicious treat?”

The first time I served these cookies, my friends and family were amazed. They couldn’t believe how the pineapple and brown sugar created such a wonderful caramelized topping on the cookies, and the maraschino cherry added the perfect touch of color and sweetness. They were a huge hit! Now, every time I make these cookies, they disappear in minutes. They’ve become a must-have at my holiday parties and family gatherings, and I know they’ll quickly become a favorite in your home as well.

Why This Pineapple Upside Down Sugar Cookies:

  • Tropical Flavor: The combination of pineapple, brown sugar, and maraschino cherries gives these cookies a tropical flair that’s both sweet and tangy.
  • Fun Twist: These cookies take the traditional pineapple upside-down cake and make it into a fun, portable treat that’s perfect for any occasion.
  • Easy to Make: With simple ingredients and a quick baking time, these cookies are easy to prepare, making them a great option for busy bakers.
  • Visually Stunning: The vibrant colors of the pineapple and cherry topping make these cookies as beautiful as they are delicious.
  • Versatile: While perfect for the holidays, these cookies are also great for summer parties, BBQs, or just as a special snack anytime.

What You Need For Pineapple Upside Down Sugar Cookies:

For the cookies:

  • 2 ½ cups all-purpose flour
  • 1 teaspoon baking soda
  • ¼ teaspoon salt
  • 1 cup unsalted butter, softened
  • 1 cup granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 2 tablespoons milk

For the topping:

  • 8-10 pineapple rings (fresh or canned), drained and cut into halves or quarters
  • 2 tablespoons brown sugar
  • 10 maraschino cherries, stems removed

How to Make Pineapple Upside Down Sugar Cookies:

  1. Preheat the oven: Preheat your oven to 350°F (175°C). Line two baking sheets with parchment paper or silicone baking mats.
  2. Prepare the cookie dough: In a medium bowl, whisk together the flour, baking soda, and salt. In a large mixing bowl, cream together the softened butter and granulated sugar until light and fluffy. Add the egg, vanilla extract, and milk, and beat until combined. Gradually add the dry ingredients and mix until just combined.
  3. Shape the cookie dough: Scoop tablespoon-sized portions of dough and roll them into balls. Place the dough balls onto the prepared baking sheets, spacing them about 2 inches apart.
  4. Prepare the topping: Gently press the dough balls down slightly with the back of a spoon to flatten them. Take half of a pineapple ring and place it in the center of each cookie dough ball. Sprinkle each pineapple ring with a small amount of brown sugar. Place a maraschino cherry on top of each pineapple ring.
  5. Bake the cookies: Bake the cookies for 12-15 minutes or until the edges are golden brown. Remove the cookies from the oven and let them cool on the baking sheet for a few minutes before transferring them to a wire rack to cool completely.
  6. Serve and enjoy: These cookies are best served fresh, but you can store them in an airtight container for up to 3 days.

Tips for Pineapple Upside Down Sugar Cookies:

  • Don’t overbake: Be careful not to overbake the cookies, as they should be soft and chewy with a slight golden edge.
  • Canned pineapple works well: If fresh pineapple isn’t available, canned pineapple rings work perfectly. Just make sure to drain them thoroughly to avoid excess moisture.
  • Adjust sweetness: If you like a sweeter cookie, add a little more brown sugar to the topping, or drizzle with extra caramel sauce once they’re baked.
  • Pineapple alternatives: If you prefer a different fruit, try substituting the pineapple with peaches, apricots, or even cherries for a ifferent twist.

Substitutions and Variations:

  • Gluten-Free: Use a gluten-free all-purpose flour blend to make these cookies gluten-free.
  • Dairy-Free: Use dairy-free butter and a non-dairy milk, like almond or coconut milk, to make this recipe dairy-free.
  • Different Toppings: While pineapple is traditional, you can experiment with other fruits such as strawberries or mango for a unique flavor combination.

Make a Healthier Version:

  • Reduced-Sugar: Use a sugar substitute like Stevia or Monk Fruit in place of the granulated sugar and brown sugar for a lower-sugar version.
  • Whole Wheat Flour: Use whole wheat flour instead of all-purpose flour for added fiber and a slightly nuttier flavor.
  • Less Butter: Reduce the butter amount by half or use a butter substitute like applesauce for a lighter version.

Closing for Pineapple Upside Down Sugar Cookies:

And there you have it! Pineapple Upside Down Sugar Cookies are the perfect blend of sweet and tangy tropical flavors in a fun, easy-to-make cookie. Whether you’re looking for something new to bake this holiday season or you want a fresh treat for a summer picnic, these cookies are sure to be a hit. The combination of the pineapple, cherry, and caramelized brown sugar creates a mouthwatering treat that will have everyone asking for the recipe. Let us know how your cookies turn out, and be sure to check out more of our delicious, tropical-inspired recipes!

Frequently Asked Questions For Pineapple Upside Down Sugar Cookies:

  1. Can I use fresh pineapple instead of canned?
    Yes, you can use fresh pineapple. Just be sure to cut it into small pieces and remove any excess moisture before using it as a topping.
  2. Can I make these cookies ahead of time?
    Yes, you can bake the cookies and store them in an airtight container for up to 3 days. They’re best served fresh but will still be delicious the next day.
  3. Can I freeze these cookies?
    Yes, you can freeze these cookies for up to 1 month. To freeze, let them cool completely, then place them in a single layer on a baking sheet. Once frozen, transfer to an airtight container.
  4. What can I use as a substitute for maraschino cherries?
    You can use fresh cherries, candied cherries, or even small red gumdrops for a fun alternative.
  5. Can I make these cookies gluten-free?
    Yes, you can substitute the all-purpose flour with a gluten-free flour blend for a gluten-free version of these cookies.
  6. Can I add nuts to the topping?
    Yes! Chopped pecans or walnuts would add a lovely crunch to the cookies. Sprinkle them on top along with the brown sugar and pineapple.
  7. Can I use a different type of sugar?
    Yes, you can use coconut sugar or even a sugar substitute like Stevia for a lower-calorie version.
  8. Do I need to chill the dough before baking?
    No, there’s no need to chill the dough for these cookies. They bake perfectly without chilling.
  9. Can I make these cookies dairy-free?
    Yes, just use dairy-free butter and a plant-based milk like almond milk.
  10. How do I store leftover cookies?
    Store leftover cookies in an airtight container at room temperature for up to 3 days.
  11. Can I make these cookies without eggs?
    Yes, you can use an egg substitute like flaxseed meal or chia seeds mixed with water to make these cookies egg-free.
  12. How can I make the cookies chewier?
    To make the cookies chewier, slightly underbake them or add a tablespoon of honey or corn syrup to the dough.
  13. Can I decorate the cookies with frosting?
    Yes! You can drizzle the cookies with a simple glaze or frosting for extra sweetness and decoration.
  14. How can I make the topping less sweet?
    If you prefer a less sweet topping, use less brown sugar on the pineapple and omit the maraschino cherries.
  15. Can I double the recipe?
    Yes, you can double the recipe to make a larger batch of cookies.
  16. Can I use a different fruit for the topping?
    Yes, you can experiment with other fruits like peaches, mangoes, or apricots for a different flavor.

These Pineapple Upside Down Sugar Cookies are the perfect tropical treat for any occasion. Enjoy them with family and friends this holiday season or whenever you need a sweet, fruity snack!

Pineapple Upside Sugar Cookies

0 from 0 votes
Recipe by Alexandra Course: All Word Recipes
Servings

4

servings
Prep time

30

minutes
Cooking time

40

minutes
Calories

300

kcal
Total time

0

minutes
Cook Mode

Keep the screen of your device on

Ingredients

  • For the cookies:
  • 2 2 ½ cups all-purpose flour

  • 1 teaspoon 1 baking soda

  • ¼ teaspoon salt

  • 1 cup 1 unsalted butter, softened

  • 1 cup 1 granulated sugar

  • 1 large 1 egg

  • 1 teaspoon 1 vanilla extract

  • 2 tablespoons 2 milk

  • For the topping:
  • 8 8 -10 pineapple rings (fresh or canned), drained and cut into halves or quarters

  • 2 tablespoons 2 brown sugar

  • 10 10 maraschino cherries, stems removed

Directions

  • Preheat the oven: Preheat your oven to 350°F (175°C). Line two baking sheets with parchment paper or silicone baking mats.
  • Prepare the cookie dough: In a medium bowl, whisk together the flour, baking soda, and salt. In a large mixing bowl, cream together the softened butter and granulated sugar until light and fluffy. Add the egg, vanilla extract, and milk, and beat until combined. Gradually add the dry ingredients and mix until just combined.
  • Shape the cookie dough: Scoop tablespoon-sized portions of dough and roll them into balls. Place the dough balls onto the prepared baking sheets, spacing them about 2 inches apart.
  • Prepare the topping: Gently press the dough balls down slightly with the back of a spoon to flatten them. Take half of a pineapple ring and place it in the center of each cookie dough ball. Sprinkle each pineapple ring with a small amount of brown sugar. Place a maraschino cherry on top of each pineapple ring.
  • Bake the cookies: Bake the cookies for 12-15 minutes or until the edges are golden brown. Remove the cookies from the oven and let them cool on the baking sheet for a few minutes before transferring them to a wire rack to cool completely.
  • Serve and enjoy: These cookies are best served fresh, but you can store them in an airtight container for up to 3 days.

Follow US on Pinterest

Follow @middleeastsector on Pinterest

Share via
Send this to a friend