Introduction and Origin
Pineapple Upside Sugar Cookies are a playful and tropical twist on the classic pineapple upside-down cake. Inspired by the retro dessert that became popular in the mid-20th century, these cookies capture the nostalgic flavors of caramelized pineapple and cherry, layered with the soft, buttery goodness of a sugar cookie. It’s a handheld treat that combines familiarity with fresh, sunny flavor.
Cultural Significance
The original pineapple upside-down cake holds a special place in American baking history, often associated with potlucks, Sunday suppers, and holiday celebrations. These cookies echo that warm sense of community, family, and tradition while adding a modern, convenient spin. They’re perfect for celebrations, bake sales, or simply bringing a little joy into everyday life.
Ingredients Quantity
For the Cookie Dough:
- 1 cup unsalted butter, softened
- 1 cup granulated sugar
- 1 large egg
- 1 teaspoon vanilla extract
- 2 1/4 cups all-purpose flour
- 1/2 teaspoon baking soda
- 1/2 teaspoon baking powder
- 1/4 teaspoon salt
For the Topping:
- 1/2 cup brown sugar (light or dark)
- 12 pineapple rings (canned, well-drained and patted dry)
- 12 maraschino cherries
Optional Additions
- A pinch of cinnamon in the dough for warmth
- Coconut flakes sprinkled over the topping for tropical flair
- A splash of pineapple juice in the dough for enhanced flavor
- A drizzle of icing or glaze for extra sweetness
Tips for Success
- Drain and dry pineapple well: Excess moisture can affect the cookie texture. Pat dry with paper towels before using.
- Chill the dough: This helps control spreading and ensures soft, chewy cookies.
- Use parchment paper or silicone mats: Helps prevent sticking from the caramelized topping.
- Flatten slightly before baking: This helps the cookies bake more evenly and hold the topping.
- Cool before removing: Let the cookies cool slightly on the tray so the topping can set and not slide off.
Instructions
- Preheat oven to 350°F (175°C). Line baking sheets with parchment paper.
- Prepare the topping: Sprinkle a small amount of brown sugar in the center of each parchment-lined cookie spot. Place a pineapple ring on top, and add a cherry in the center.
- Make the cookie dough: In a large bowl, cream together butter and granulated sugar until fluffy. Add egg and vanilla extract, mixing well.
- In a separate bowl, whisk together flour, baking soda, baking powder, and salt. Gradually add dry ingredients to the butter mixture until fully combined.
- Scoop the dough: Roll into 2-tablespoon balls and flatten slightly. Place on top of the pineapple rings, pressing gently to adhere.
- Bake for 12–15 minutes, or until edges are golden and centers are set.
- Cool on the tray for 5 minutes, then transfer to a wire rack to cool completely.
Description
Pineapple Upside Sugar Cookies are a delightful mash-up of classic and creative. The cookie base is soft, rich, and buttery, with just the right chew. The caramelized pineapple adds juicy sweetness, and the cherry center gives each bite a pop of color and flavor. It’s the joy of pineapple upside-down cake, simplified into a cookie that’s easy to share and hard to resist.
Nutritional Information (Per Cookie, based on 12 servings)
- Calories: ~210
- Total Fat: 10g
- Saturated Fat: 6g
- Cholesterol: 35mg
- Sodium: 90mg
- Total Carbohydrates: 28g
- Sugars: 18g
- Dietary Fiber: <1g
- Protein: 2g
Values may vary depending on specific brands and ingredients used.
Conclusion and Recommendation
If you love tropical flavors, nostalgic desserts, or just trying something fun and new, Pineapple Upside Sugar Cookies are a must-bake. They’re simple enough for casual baking and special enough for guests. Sweet, soft, and sunny, these cookies are a treat that bridges tradition and creativity.
Embracing Healthful Indulgence
To enjoy these cookies with a health-conscious twist, try reducing the sugar slightly, using whole wheat pastry flour, or replacing butter with a plant-based alternative. You can also experiment with fresh pineapple or skip the cherry to cut down on added sugars. Healthful indulgence is about enjoying what you love—thoughtfully and in moderation.