Pineapple Upside Down Sugar Cookies

 

Introduction

Get ready to transform your dessert table with a cookie that’s as delightful to look at as it is to eat: Pineapple Upside Down Sugar Cookies! Forget everything you thought you knew about traditional sugar cookies; we’re taking the beloved buttery classic and giving it a vibrant, sun-soaked, tropical makeover. Inspired by the iconic pineapple upside-down cake, these cookies feature a sweet, tender sugar cookie base crowned with a caramelized pineapple ring, a juicy maraschino cherry, and a sprinkle of toasted coconut. It’s a playful and sophisticated twist that promises to be the star of any gathering, from backyard BBQs to elegant tea parties, or simply a unique treat to brighten your day.

The magic of these cookies lies in their “upside-down” assembly. Instead of placing the fruit on top after baking, we arrange the vibrant pineapple and cherry directly on the baking sheet, press the sugar cookie dough gently over them, and then bake. As they bake, the fruit caramelizes slightly, infusing the cookie with its sweet and tangy essence, and creating that signature glistening topping. Once cooled and flipped, you’re greeted with a miniature masterpiece, each cookie a perfect individual serving of tropical bliss. The combination of the soft, chewy cookie, the bright, slightly tart pineapple, the sweet pop of the cherry, and the subtle crunch of coconut creates a symphony of flavors and textures that will have everyone asking for the recipe.

These Pineapple Upside Down Sugar Cookies are more than just a dessert; they’re an experience. They’re visually stunning, bursting with flavor, and surprisingly fun to make. Whether you’re a seasoned baker looking for a creative challenge or a beginner eager to impress, this recipe offers a rewarding journey into the world of elevated cookie baking. Prepare to fall in love with your new favorite tropical indulgence!

Nutritional Information

Per serving (approximate values):

• Calories: 180 kcal
• Protein: 2g
• Carbohydrates: 25g
• Fat: 9g
• Fiber: 1g
• Sodium: 80mg

Ingredients

• 1 cup (2 sticks) unsalted butter, softened
• 1 ½ cups granulated sugar, plus 2 tablespoons for topping
• 2 large eggs
• 1 teaspoon vanilla extract
• 3 cups all-purpose flour
• 1 teaspoon baking powder
• ½ teaspoon salt
• 1 (20-ounce) can pineapple rings in light syrup, drained and patted very dry
• 1 (10-ounce) jar maraschino cherries, drained and patted very dry
• ½ cup shredded unsweetened coconut, optional

Instructions

1. Prepare the Cookie Dough: In a large mixing bowl, cream together the softened butter and 1 ½ cups of granulated sugar until light and fluffy, about 2-3 minutes.
2. Beat in the eggs one at a time, incorporating each fully before adding the next. Stir in the vanilla extract.
3. In a separate medium bowl, whisk together the all-purpose flour, baking powder, and salt.
4. Gradually add the dry ingredients to the wet ingredients, mixing on low speed until just combined and a soft dough forms. Do not overmix.
5. Divide the dough into two equal portions, flatten slightly into discs, wrap tightly in plastic wrap, and refrigerate for at least 1 hour, or up to 24 hours. Chilling the dough is crucial for easier handling and to prevent excessive spreading.
6. Preheat Oven and Prepare Baking Sheets: Preheat your oven to 375°F (190°C). Line two large baking sheets with parchment paper. This is essential to prevent sticking and for easy removal of the cookies.
7. Prepare the Pineapple and Cherries: Open the can of pineapple rings. Drain them thoroughly and then pat each ring very dry with paper towels. Excess moisture will make your cookies soggy. Using a 2 ½ to 3-inch round cookie cutter (or a knife), cut each pineapple ring into smaller, cookie-sized circles. You should get about 12-16 small rings from a standard can.
8. Drain the maraschino cherries and pat them very dry with paper towels.
9. Assemble the “Upside Down” Topping: Arrange the cut pineapple circles on the prepared baking sheets, leaving about 2 inches between each piece.
10. Place one maraschino cherry in the center of each pineapple circle.
11. If using, sprinkle about ½ teaspoon of shredded coconut around the pineapple and cherry on each spot.
12. Sprinkle about ¼ teaspoon of the remaining 2 tablespoons of granulated sugar directly over the pineapple and cherry on each spot. This will help with caramelization.
13. Add the Cookie Dough: Remove one disc of chilled cookie dough from the refrigerator. On a lightly floured surface, roll out the dough to about ¼-inch thickness.
14. Using the same 2 ½ to 3-inch round cookie cutter you used for the pineapple (or one slightly larger than your pineapple pieces), cut out cookie dough circles.
15. Carefully lift each cookie dough circle and gently place it directly on top of a prepared pineapple and cherry assembly on the baking sheet, pressing down lightly to adhere the dough to the fruit. Ensure the dough fully covers the fruit.
16. Repeat with the remaining dough and fruit, re-rolling scraps as needed.
17. Bake the Cookies: Bake for 10-14 minutes, or until the edges of the cookies are lightly golden brown. The baking time may vary depending on your oven and the thickness of your cookies.
18. Cool and Serve: Once baked, remove the baking sheets from the oven. Let the cookies cool on the baking sheets for 5-7 minutes. This allows the caramelized topping to set and makes them easier to handle.
19. After partial cooling, carefully use a thin spatula to lift each cookie and flip it over onto a wire rack to cool completely, revealing the beautiful pineapple and cherry topping.
20. Serve warm or at room temperature.

Cooking Tips and Variations

For the best results, always ensure your butter is truly softened for creaming, but not melted. This creates the proper texture for the cookie dough. When preparing the pineapple and cherries, don’t underestimate the importance of thoroughly draining and patting them dry. Any excess moisture will release during baking, potentially making your cookies soggy in the center. If you’re short on time, you can briefly microwave the canned pineapple slices for 10-15 seconds and then pat them dry; this helps remove stubborn moisture. For a more intense caramelized flavor, you can lightly brush the pineapple with a tiny amount of melted butter and a pinch of brown sugar before placing the dough on top, though the recipe works beautifully without this extra step. Always use parchment paper on your baking sheets; the caramelized sugars from the pineapple can stick tenaciously to unlined sheets, making removal difficult and potentially damaging your beautiful cookies. Don’t overcrowd your baking sheets; leave enough space for air circulation and for the cookies to spread slightly without touching. Baking in batches is often better than trying to fit too many on one sheet.

If you’re looking to play with variations, the possibilities are delicious! For a different fruit profile, consider using thinly sliced canned peaches or apricots, ensuring they are also well-drained. Each will offer a unique flavor and visual appeal. You could also experiment with other small, firm fruits like kiwi slices (though these may release more moisture). To enhance the coconut flavor, lightly toast your shredded coconut in a dry skillet over medium-low heat until golden brown and fragrant before sprinkling it on the cookies; this adds a deeper, nuttier dimension. While these cookies are fantastic on their own, a light coconut glaze made from powdered sugar, coconut milk, and a touch of vanilla or coconut extract drizzled over the cooled cookies would add another layer of sweetness and moisture. Alternatively, a simple lime glaze (powdered sugar and fresh lime juice) would offer a bright, zesty contrast to the sweet fruit. For those who enjoy a hint of spice, a pinch of ground nutmeg or cardamom added to the cookie dough would complement the tropical flavors beautifully. You can also vary the size of your cookies; just adjust the pineapple cutting and baking time accordingly. For miniature versions, use tiny pineapple rings and a smaller cookie cutter. Always allow the cookies to cool on the baking sheet for a few minutes before flipping; this lets the caramelized fruit topping firm up, preventing it from sticking or breaking when transferred.

Storage and Reheating

To store your Pineapple Upside Down Sugar Cookies, allow them to cool completely before placing them in an airtight container. If stacking, it’s best to place a piece of parchment paper between layers to prevent the delicate caramelized topping from sticking or transferring. Store at room temperature for up to 3-4 days. For longer storage, you can refrigerate them for up to a week. The texture of the cookie may soften slightly when refrigerated, but the flavors will remain vibrant.

These cookies are best enjoyed at room temperature, but if you prefer them slightly warm, you can gently reheat them. To reheat, place the cookies on a baking sheet and warm them in a preheated oven at 275°F (135°C) for about 5-7 minutes, or until just warmed through. Be careful not to overheat, as this can dry out the cookies. Alternatively, you can microwave individual cookies for 10-15 seconds, but be aware that microwaving can sometimes alter the texture of the cookie, making it softer or chewier than desired. For the best flavor and texture, room temperature or a gentle oven reheat is recommended.

Frequently Asked Questions

Can I use fresh pineapple instead of canned?

While fresh pineapple can be used, it contains significantly more moisture than canned pineapple. If opting for fresh, slice it very thinly and then pat it extremely dry with paper towels. You might even want to bake the pineapple slices on their own for a few minutes before placing the cookie dough on top to dry them out further. However, canned pineapple is generally recommended for its consistent moisture content and ease of use in this recipe.

My cookies are sticking to the parchment paper after baking. What went wrong?

If your cookies are sticking, it’s likely due to the caramelized sugars from the pineapple. Ensure you are using good quality parchment paper. Also, allowing the cookies to cool on the baking sheet for the recommended 5-7 minutes is crucial. This cooling period allows the sugars to firm up. If they still stick, you might try lightly greasing the parchment paper before placing the pineapple, or carefully running a thin, offset spatula underneath while they are still slightly warm.

Can I freeze these cookies?

Yes, these cookies can be frozen. Once completely cooled, place them in a single layer on a baking sheet and freeze for about an hour until firm. Then, transfer them to an airtight freezer-safe container. You can layer them with parchment paper in between. They will keep in the freezer for up to 2-3 months. Thaw at room temperature or in the refrigerator before serving. The texture of the pineapple might be slightly softer after thawing, but the flavor will still be delicious.