Pineapple Upside Down Sugar Cookies That Delight Every Bite

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Update : May 3, 2026

Delicious pineapple upside down cookies decorated on a plate

why make this recipe

Pineapple Upside Down Sugar Cookies are a delightful twist on a classic dessert. These cookies bring together the sweetness of sugar cookies with the tropical flavor of pineapple. They are fun, easy to make, and perfect for any occasion. With their soft texture and chewy bite, each cookie is a little piece of paradise. Plus, they look lovely with the pineapple rings on top, making them ideal for gatherings or just as a sweet treat at home.

how to make Pineapple Upside Down Sugar Cookies

Making these cookies is simple and requires just a few steps. Here’s how to create these tasty delights.

Ingredients:

  • 1 cup unsalted butter (softened)
  • 1 cup granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract (optional)
  • 2 cups all-purpose flour (or gluten-free blend)
  • 1 teaspoon baking soda
  • 1/2 teaspoon salt
  • 1 can canned pineapple rings (well-drained)
  • 2 tablespoons additional sugar for sprinkling

Directions:

  1. Preheat your oven to 350°F (175°C).
  2. In a large bowl, cream together the softened butter and granulated sugar until light and fluffy.
  3. Add the egg and vanilla extract (if using) to the bowl. Mix until well combined.
  4. In another bowl, whisk the flour, baking soda, and salt.
  5. Gradually add the dry ingredients to the wet mixture, mixing until the dough comes together.
  6. Line a baking sheet with parchment paper.
  7. Place a pineapple ring on each spot where you want a cookie. If you like, you can cut the rings in half and place them against each other for a nice look.
  8. Spoon cookie dough into the center of each pineapple ring.
  9. Sprinkle a little sugar on top of each cookie before baking.
  10. Bake in the preheated oven for about 12-15 minutes or until the edges are golden.
  11. Allow them to cool on the baking sheet for a few minutes, then transfer to a wire rack.

how to serve Pineapple Upside Down Sugar Cookies

These cookies can be served warm or at room temperature. They are perfect on their own or can be paired with a scoop of vanilla ice cream for an extra treat. You can also garnish them with some fresh mint leaves for a pop of color.

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 about 4-5 days. If you want to keep them longer, consider freezing them. Wrap each cookie in plastic wrap and place them in a freezer bag. They can be frozen for up to 3 months. Just thaw them at room temperature when you want to enjoy them.

tips to make Pineapple Upside Down Sugar Cookies

  • Make sure the butter is softened for easy mixing.
  • Drain the pineapple well to prevent excess liquid in the cookies.
  • Adjust the baking time based on your oven, as some may bake faster than others. Keep an eye on the edges for doneness.
  • Experiment with adding nuts or coconut for an added crunch and flavor.

variation

You can try using other fruits, such as peaches or cherries, instead of pineapple. This variation will give you a different flavor but keep the same delicious cookie base.

FAQs

1. Can I use fresh pineapple instead of canned?
Yes, fresh pineapple can be used! Just make sure to slice it thinly and remove excess moisture.

2. Can I make these cookies gluten-free?
Absolutely! You can replace the all-purpose flour with a gluten-free flour blend.

3. How can I make these cookies more chewy?
To achieve a chewier texture, try reducing the baking time slightly and adding an extra egg yolk to the recipe.

Print

Pineapple Upside Down Sugar Cookies

Delightful sugar cookies topped with pineapple rings, bringing together tropical flavors and a soft, chewy texture.

  • Prep Time: 15 minutes
  • Cook Time: 15 minutes
  • Total Time: 30 minutes
  • Yield: 12 cookies 1x
  • Category: Dessert
  • Method: Baking
  • Cuisine: American
  • Diet: Vegetarian

Ingredients

Scale
  • 1 cup unsalted butter (softened)
  • 1 cup granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract (optional)
  • 2 cups all-purpose flour (or gluten-free blend)
  • 1 teaspoon baking soda
  • 1/2 teaspoon salt
  • 1 can canned pineapple rings (well-drained)
  • 2 tablespoons additional sugar for sprinkling

Instructions

  1. Preheat your oven to 350°F (175°C).
  2. Cream together the softened butter and granulated sugar until light and fluffy.
  3. Add the egg and vanilla extract (if using) to the bowl. Mix until well combined.
  4. Whisk the flour, baking soda, and salt in another bowl.
  5. Gradually add the dry ingredients to the wet mixture, mixing until the dough comes together.
  6. Line a baking sheet with parchment paper.
  7. Place a pineapple ring on each spot where you want a cookie.
  8. Spoon cookie dough into the center of each pineapple ring.
  9. Sprinkle a little sugar on top of each cookie before baking.
  10. Bake for about 12-15 minutes or until the edges are golden.
  11. Allow them to cool on the baking sheet for a few minutes, then transfer to a wire rack.

Notes

Store cookies in an airtight container at room temperature for 4-5 days or freeze for up to 3 months.

Nutrition

  • Serving Size: 1 cookie
  • Calories: 150
  • Sugar: 8g
  • Sodium: 100mg
  • Fat: 7g
  • Saturated Fat: 4g
  • Unsaturated Fat: 2g
  • Trans Fat: 0g
  • Carbohydrates: 20g
  • Fiber: 0g
  • Protein: 2g
  • Cholesterol: 30mg

Keywords: cookies, pineapple, dessert, baking, tropical

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