Pineapple Upside-Down Sugar Cookies
Pineapple Upside-Down Sugar Cookies are a fun twist on a classic dessert! These delightful treats combine the tropical goodness of pineapple and the sweetness of sugar cookies. With their bright colors and unique presentation, they are perfect for any occasion, from parties to casual family gatherings.
Why Make This Recipe
Making Pineapple Upside-Down Sugar Cookies is a great way to enjoy a twist on two beloved desserts. These cookies bring nostalgia with their pineapple and cherry topping while offering the chewy texture of a cookie. They are easy to prepare, and the fun process of baking them in a muffin tin adds a creative touch. Everyone will love the burst of flavors, making these cookies a hit at any event!
How to Make Pineapple Upside-Down Sugar Cookies
Ingredients:
- 1/2 cup unsalted butter, melted
- 3/4 cup brown sugar, packed
- 1 can (20 oz) pineapple rings, drained
- 12 maraschino cherries
- 2 1/2 cups all-purpose flour
- 1 teaspoon baking soda
- 1/2 teaspoon salt
- 1 cup unsalted butter, softened
- 1 1/4 cups granulated sugar
- 1 large egg
- 1 teaspoon vanilla extract
Directions:
Step 1: Preheat your oven to 350°F (175°C). Lightly grease a standard muffin tin or line it with silicone liners.
Step 2: Place 1 teaspoon of melted butter into each muffin cup. Sprinkle 1 tablespoon of brown sugar into each cup. Add a pineapple ring (or half if using smaller cups) to each cup and place a maraschino cherry in the center.
Step 3: 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 (about 2-3 minutes). Add the egg and vanilla extract, mixing until combined. Gradually add the flour mixture, mixing just until combined.
Step 4: Scoop about 2 tablespoons of cookie dough and gently press it over the pineapple and brown sugar layer in each muffin cup.
Step 5: Bake for 15-18 minutes or until the cookies are golden brown and set. Allow the cookies to cool in the pan for 5-10 minutes before inverting them onto a wire rack.
Step 6: Let the cookies cool slightly before serving. Enjoy warm or at room temperature.
How to Serve Pineapple Upside-Down Sugar Cookies
Serve Pineapple Upside-Down Sugar Cookies as a sweet dessert or a fun snack. They are delicious on their own and pair wonderfully with a scoop of vanilla ice cream or a dollop of whipped cream. For a festive touch, sprinkle some shredded coconut or chopped nuts on top before serving.
How to Store Pineapple Upside-Down Sugar Cookies
To store these cookies, place them in an airtight container at room temperature. They will stay fresh for up to 3 days. If you want to keep them longer, you can freeze them for up to a month. Just thaw them at room temperature before serving!
Tips to Make Pineapple Upside-Down Sugar Cookies
- Make sure the butter is softened properly to get a light and fluffy texture.
- If you don’t have pineapple rings, you can use crushed pineapple, but be sure to drain it well.
- Feel free to adjust the amount of brown sugar or add a sprinkle of cinnamon for extra flavor.
Variation
You can experiment with other fruits like peaches or cherries instead of pineapple. You could also try adding some nuts or chocolate chips to the cookie dough for added texture and taste.
FAQs
1. Can I use fresh pineapple instead of canned?
Yes, fresh pineapple can be used. Just slice it into rings and make sure to remove the core.
2. What if I don’t have a muffin tin?
You can use any oven-proof dish to bake these cookies, but the shape and presentation will be different.
3. How can I make these cookies less sweet?
You can reduce the amount of brown sugar in the recipe if you prefer a less sweet cookie.

Pineapple Upside-Down Sugar Cookies
- Total Time: 33 minutes
- Yield: 12 servings 1x
- Diet: Vegetarian
Description
A fun twist on classic sugar cookies featuring a tropical pineapple topping.
Ingredients
- 1/2 cup unsalted butter, melted
- 3/4 cup brown sugar, packed
- 1 can (20 oz) pineapple rings, drained
- 12 maraschino cherries
- 2 1/2 cups all-purpose flour
- 1 teaspoon baking soda
- 1/2 teaspoon salt
- 1 cup unsalted butter, softened
- 1 1/4 cups granulated sugar
- 1 large egg
- 1 teaspoon vanilla extract
Instructions
- Preheat your oven to 350°F (175°C). Lightly grease a standard muffin tin or line it with silicone liners.
- Place 1 teaspoon of melted butter into each muffin cup. Sprinkle 1 tablespoon of brown sugar into each cup. Add a pineapple ring (or half if using smaller cups) to each cup and place a maraschino cherry in the center.
- 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 (about 2-3 minutes). Add the egg and vanilla extract, mixing until combined. Gradually add the flour mixture, mixing just until combined.
- Scoop about 2 tablespoons of cookie dough and gently press it over the pineapple and brown sugar layer in each muffin cup.
- Bake for 15-18 minutes or until the cookies are golden brown and set. Allow the cookies to cool in the pan for 5-10 minutes before inverting them onto a wire rack.
- Let the cookies cool slightly before serving. Enjoy warm or at room temperature.
Notes
Store in an airtight container at room temperature for up to 3 days or freeze for up to a month.
- Prep Time: 15 minutes
- Cook Time: 18 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
Nutrition
- Serving Size: 1 cookie
- Calories: 200
- Sugar: 15g
- Sodium: 150mg
- Fat: 8g
- Saturated Fat: 5g
- Unsaturated Fat: 3g
- Trans Fat: 0g
- Carbohydrates: 28g
- Fiber: 1g
- Protein: 2g
- Cholesterol: 30mg
Keywords: cookies, dessert, pineapple, sugar cookies, baking
