Pineapple Upside Down Sugar Cookies

By lbc14
October 18, 2026

How to make Pineapple Upside Down Sugar Cookies

Ingredients:

  • For the Cookies:

    Pineapple Upside Down Sugar Cookies
    • 1 cup unsalted butter, softened
    • 1 cup granulated sugar
    • 1 large egg
    • 1 teaspoon vanilla extract
    • 2 cups all-purpose flour
    • 1/2 teaspoon baking soda
    • 1/2 teaspoon salt
  • For the Topping:

    • 1 can (20 oz) sliced pineapple, drained
    • 1/2 cup brown sugar, packed
    • Maraschino cherries (optional, for garnish)

Directions:

  1. Preheat the oven to 350°F (175°C). Line a baking sheet with parchment paper.

  2. Make the Cookie Dough:

    • In a large bowl, cream together the softened butter and granulated sugar until light and fluffy.
    • Beat in the egg and vanilla extract until well combined.
  3. Mix Dry Ingredients:

    • In another bowl, whisk together flour, baking soda, and salt.
    • Gradually add the dry mixture to the wet mixture, mixing until just combined.
  4. Prepare the Topping:

    • In a small saucepan over medium heat, melt the brown sugar with a splash of water.
    • Add the drained pineapple slices and cook for a few minutes until they are slightly caramelized.
  5. Assemble the Cookies:

    • Place about a tablespoon of cookie dough on the prepared baking sheet.
    • Gently press a caramelized pineapple slice on top of each cookie dough mound.
    • If using cherries, place one cherry in the center of each pineapple slice.
  6. Bake:

    • Bake in the preheated oven for 12-15 minutes or until the edges are lightly golden.
    • Let the cookies cool on the baking sheet for a few minutes before transferring them to a wire rack.
  7. Serve: Enjoy the cookies warm, or let them cool completely before storing.

Why You’ll Love This Pineapple Upside Down Sugar Cookies

Pineapple Upside Down Sugar Cookies bring a unique twist to the classic pineapple upside-down cake. The beautiful caramelized pineapple and the butteriness of the cookies create a perfect pairing. Each bite is soft, chewy, and bursting with pineapple flavor. The sweetness of brown sugar complements the natural tang of pineapple, making these cookies a delightful treat. They are not just delicious, but also visually appealing, turning any gathering into a festive occasion.

Nutritional Benefits

Pineapple is rich in vitamins and minerals. It provides a good source of vitamin C, which helps boost the immune system. The fruit is also high in manganese, which is important for bone health. The cookies, made primarily from sugar and butter, should be enjoyed in moderation, but they still offer a joyful, sweet experience alongside the beneficial properties of pineapple.

What to Serve With Pineapple Upside Down Sugar Cookies

These cookies pair excellently with a variety of beverages. You can serve them with:

  • Coffee or Tea: A warm cup of coffee or aromatic tea complements the sweetness of the cookies.
  • Ice Cream: Vanilla or coconut ice cream served alongside adds a creamy contrast.
  • Fruit Juices: A refreshing glass of pineapple juice or lemonade pairs wonderfully.
  • Milkshakes: Creamy pineapple or vanilla milkshakes enhance the flavor experience.

How to store Pineapple Upside Down Sugar Cookies

To keep your cookies fresh, store them in an airtight container at room temperature. They should last for about a week. If you want to store them for longer, consider placing them in the refrigerator, where they can stay good for up to two weeks. For an even longer shelf life, you can freeze the cookies. Wrap them tightly in plastic wrap and then place them inside a freezer-safe container. They will maintain their quality for up to three months. Just remember to thaw them at room temperature before enjoying!

Tips and Mistakes to Avoid

  1. Cream the Butter and Sugar Well: Don’t skip the creaming step; it helps incorporate air into the dough for a lighter texture.

  2. Don’t Overmix: Once you combine the wet and dry ingredients, mix just until combined to avoid tough cookies.

  3. Check the Oven Temperature: Use an oven thermometer to make sure your oven temperature is accurate. Oven temperatures can vary, affecting baking time.

  4. Pineapple Preparation: Ensure your pineapple slices are well-drained to avoid soggy cookies.

  5. Spacing on the Baking Sheet: Leave enough space between the cookies on the baking sheet. They will spread during baking.

Variation

Feel free to experiment with different toppings! Instead of pineapple, you can use:

  • Peaches: Fresh or canned peaches can provide a sweet and juicy bite.
  • Cherries: Cherries can be a delightful swap, especially paired with chocolate chunks.
  • Strawberries: Fresh strawberry slices can add a fresh and fruity touch.
  • Use Coconut: Add some shredded coconut to the cookie dough for a tropical flavor boost.

FAQs

1. Can I use fresh pineapple instead of canned?
Yes, you can use fresh pineapple. Just make sure to slice it thinly and cook it slightly to achieve that caramelized texture.

2. Can I make these cookies gluten-free?
Yes, you can substitute regular flour with a gluten-free flour blend. Just ensure that your chosen blend can substitute 1:1.

3. How many cookies does this recipe make?
This recipe generally yields around 24 cookies, depending on the size of the dough mounds you form.

Enjoy your Pineapple Upside Down Sugar Cookies as a delightful twist on the traditional dessert. They’re perfect for sharing with friends and family or enjoying as a sweet treat at any time of the day!

Pineapple Upside Down Sugar Cookies

These cookies combine the delightful flavors of pineapple upside-down cake with a soft, chewy sugar cookie base, topped with caramelized pineapple and brown sugar.
Servings 24 cookies
Prep Time 20 minutes
Cook Time 15 minutes
Total Time 35 minutes

Ingredients
  

For the Cookies

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

For the Topping

  • 1 can (20 oz) sliced pineapple, drained
  • 1/2 cup brown sugar, packed
  • Maraschino cherries (optional, for garnish)

Instructions
 

Preparation

  • Preheat the oven to 350°F (175°C). Line a baking sheet with parchment paper.
  • In a large bowl, cream together the softened butter and granulated sugar until light and fluffy.
  • Beat in the egg and vanilla extract until well combined.

Mix Dry Ingredients

  • In another bowl, whisk together flour, baking soda, and salt.
  • Gradually add the dry mixture to the wet mixture, mixing until just combined.

Prepare the Topping

  • In a small saucepan over medium heat, melt the brown sugar with a splash of water.
  • Add the drained pineapple slices and cook for a few minutes until they are slightly caramelized.

Assemble the Cookies

  • Place about a tablespoon of cookie dough on the prepared baking sheet.
  • Gently press a caramelized pineapple slice on top of each cookie dough mound.
  • If using cherries, place one cherry in the center of each pineapple slice.

Bake

  • Bake in the preheated oven for 12-15 minutes or until the edges are lightly golden.
  • Let the cookies cool on the baking sheet for a few minutes before transferring them to a wire rack.

Notes

Store cookies in an airtight container at room temperature for about a week, in the refrigerator for up to two weeks, or freeze wrapped in plastic wrap for up to three months. Thaw at room temperature before enjoying.
Calories: 150kcal
Course: Dessert, Snack
Cuisine: American
Keyword: Caramelized Pineapple, Pineapple Cookies, Sugar Cookies, Upside Down Cookies

Leave a Reply

Your email address will not be published. Required fields are marked *

Recipe Rating




Like 0
Close
Copyright © 2026 Weeknightchicken
Close