Easy Pineapple Upside Down Sugar Cookies Recipe
Introduction
These Easy Pineapple Upside Down Sugar Cookies combine the classic flavors of pineapple and cherries in a soft, buttery cookie. They’re a fun twist on the traditional upside down cake and perfect for sharing at any gathering.

Ingredients
- 2 cups all-purpose flour
- 1 cup granulated sugar
- 1/2 cup unsalted butter
- 1 egg
- 1 teaspoon baking powder
- 1/4 teaspoon salt
- 6 canned pineapple rings
- 1/2 cup brown sugar
- 12 maraschino cherries (for garnish)
Instructions
- Step 1: Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper.
- Step 2: In a mixing bowl, cream together the butter and granulated sugar until the mixture is light and fluffy.
- Step 3: Add the egg to the creamed mixture and mix well. Then, gradually incorporate the flour, baking powder, and salt until a cookie dough forms.
- Step 4: Arrange the pineapple rings on the prepared baking sheet. Place a spoonful of brown sugar in the center of each ring, then top each with a maraschino cherry.
- Step 5: Spoon cookie dough over each pineapple ring, covering the fruit and cherry.
- Step 6: Bake in the preheated oven for about 15 minutes, or until the cookies turn golden brown.
- Step 7: Remove the cookies from the oven and let them cool before serving to enjoy the full flavor.
Tips & Variations
- For extra flavor, add a teaspoon of vanilla extract to the dough before baking.
- Use fresh pineapple slices if canned aren’t available, but reduce baking time slightly to avoid excess moisture.
- Try substituting the maraschino cherries with chopped pecans or walnuts for a nutty twist.
- Chill the dough for 15 minutes before baking to help the cookies hold their shape better.
Storage
Store the cookies in an airtight container at room temperature for up to 3 days. If you want to keep them longer, refrigerate for up to a week or freeze for up to 3 months. Reheat gently in a low oven or microwave to soften before serving.
How to Serve

Serve this delicious recipe with your favorite sides.
FAQs
Can I use fresh pineapple instead of canned?
Yes, fresh pineapple works well but contains more moisture, so watch the baking time closely to avoid soggy cookies. Pat the pineapple slices dry before using.
Can these cookies be made gluten-free?
Absolutely! Substitute the all-purpose flour with a gluten-free flour blend that measures cup-for-cup for best results.
PrintEasy Pineapple Upside Down Sugar Cookies Recipe
These Easy Pineapple Upside Down Sugar Cookies combine the classic flavors of pineapple and maraschino cherries with a soft, buttery sugar cookie base. Featuring a delightful presentation with pineapple rings and cherries, these cookies are perfect for parties, special occasions, or a fun twist on traditional sugar cookies.
- Prep Time: 15 minutes
- Cook Time: 15 minutes
- Total Time: 30 minutes
- Yield: 6 servings (6 cookies) 1x
- Category: Cookies
- Method: Baking
- Cuisine: American
Ingredients
Cookie Dough
- 2 cups all-purpose flour
- 1 cup granulated sugar
- 1/2 cup unsalted butter, softened
- 1 large egg
- 1 teaspoon baking powder
- 1/4 teaspoon salt
Topping
- 6 canned pineapple rings
- 1/2 cup brown sugar
- 12 maraschino cherries (for garnish)
Instructions
- Preheat Oven: Preheat your oven to 350°F (175°C) and line a baking sheet with parchment paper to prevent sticking and ensure even baking.
- Cream Butter and Sugar: In a mixing bowl, cream together the softened unsalted butter and granulated sugar until the mixture is light and fluffy, which helps produce tender cookies.
- Add Egg and Dry Ingredients: Beat in the large egg until fully incorporated. Then gradually mix in the all-purpose flour, baking powder, and salt to form a smooth cookie dough with a balanced texture.
- Prepare Pineapple Topping: On the lined baking sheet, place a spoonful of brown sugar in the center of each canned pineapple ring. Top each pineapple ring with two maraschino cherries placed within the ring for an attractive appearance.
- Assemble Cookies: Place each pineapple ring, cherry side down, on the baking sheet. Then, scoop a generous portion of cookie dough and place it on top of each pineapple ring, covering it evenly but leaving the cherry visible.
- Bake Cookies: Bake the cookies in the preheated oven for about 15 minutes or until the cookie dough is golden brown and cooked through, indicating they are perfectly baked.
- Cool and Serve: Remove the baking sheet from the oven and allow the cookies to cool completely on a wire rack before serving. This ensures the cookies firm up and flavors meld for a delicious treat.
Notes
- You can substitute fresh pineapple rings if desired, but canned pineapple works best for consistent sweetness and moisture.
- Make sure butter is softened to room temperature for easier creaming and better cookie texture.
- Place the cherries carefully within the pineapple rings to keep them centered and visually appealing.
- For a crispier cookie, bake a couple more minutes but monitor closely to avoid burning.
- Store cooled cookies in an airtight container at room temperature for up to 3 days for maximum freshness.
Keywords: pineapple upside down cookies, sugar cookies, pineapple cookies, easy cookie recipe, maraschino cherry cookies

