Pineapple Upside Down Cookie

If you’re looking for a delightful treat that combines the nostalgic flavors of a classic dessert with the convenience of a cookie, this Pineapple Upside Down Cookie recipe is exactly what you need. These cookies capture the sweet, caramelized charm of pineapple upside down cake in a perfectly portioned bite. With a tender, buttery base and a golden topping of brown sugar, juicy crushed pineapple, and a bright maraschino cherry, they’re as visually appealing as they are delicious. Whether you’re baking for a party, a family gathering, or just a fun twist on your cookie rotation, these cookies are guaranteed to impress.

Why This Recipe Is a Must-Try

The Pineapple Upside Down Cookie offers a unique twist on the traditional cookie, combining the moist texture and tropical flavors of pineapple upside down cake. Unlike your average cookie, these have a rich caramelized top that melts in your mouth, thanks to the brown sugar and pineapple topping. The balance of tangy pineapple and sweet cherry, paired with a soft, buttery cookie, creates a flavor profile that is both nostalgic and fresh. Plus, they’re incredibly easy to make with simple pantry staples.

If you love exploring different cookie recipes, you might also enjoy experimenting with The Best Chocolate Chip Cookies, which offer a classic flavor everyone adores. But for a tropical flavor blast, Pineapple Upside Down Cookies are a game-changer.

Ingredients

• 1 cup unsalted butter, softened
• 1 cup granulated sugar
• 2 large eggs
• 1 cup all-purpose flour
• 1 teaspoon baking powder
• 1/2 teaspoon baking soda
• 1/4 teaspoon salt
• 1 teaspoon vanilla extract
• 1 cup crushed pineapple, drained
• 1/2 cup brown sugar, packed
• Maraschino cherries for topping

How To Make Pineapple Upside Down Cookie

Step 1: Prepare Your Ingredients

Begin by preheating your oven to 350°F (175°C). Line a baking sheet with parchment paper or a silicone baking mat to prevent sticking. Drain the crushed pineapple well to avoid soggy cookies, which ensures the perfect texture.

Step 2: Cream the Butter and Sugar

In a large mixing bowl, use an electric mixer to cream together the softened unsalted butter and granulated sugar until light and fluffy. This process takes about 3-4 minutes and is key to getting that tender crumb in your cookie.

Step 3: Add Eggs and Vanilla

Add the eggs one at a time, mixing well after each addition. Then stir in the vanilla extract for a warm, fragrant base.

Step 4: Combine Dry Ingredients

In a separate bowl, whisk together the all-purpose flour, baking powder, baking soda, and salt. Gradually add this dry mixture to the wet ingredients, mixing just until combined. Be careful not to overmix — you want the cookies tender, not tough.

Step 5: Shape the Cookies

Using a tablespoon or cookie scoop, drop dough balls onto the prepared baking sheet, leaving about 2 inches between each cookie.

Step 6: Add the Pineapple Topping

Press a small spoonful of drained crushed pineapple gently onto the top of each cookie. Then sprinkle about a teaspoon of packed brown sugar over the pineapple. Finally, top each cookie with one maraschino cherry, pressing it lightly into the dough.

Step 7: Bake

Bake the cookies in the preheated oven for 12-15 minutes or until the edges are lightly golden and the tops are set. The brown sugar will caramelize around the pineapple, creating that signature upside-down effect.

Step 8: Cool and Serve

Allow the cookies to cool on the baking sheet for about 5 minutes before transferring them to a wire rack to cool completely. This resting time helps the cookies firm up while keeping the pineapple juicy and delicious.

Expert Tips

• Make sure to drain the pineapple thoroughly to avoid excess moisture making your cookies soggy.
• Use room temperature butter and eggs to help the ingredients combine smoothly and create a better texture.
• If you want a more caramelized topping, try broiling the cookies for 1-2 minutes at the end of baking—watch carefully to prevent burning.
• Feel free to chill the dough for 30 minutes before baking if you want thicker cookies that hold their shape better.
• For an extra flavor boost, add a pinch of ground cinnamon or nutmeg to the dry ingredients.

Variations and Customizations

• Tropical Twist: Swap crushed pineapple for diced mango or papaya for a different fruity flavor.
• Nutty Addition: Add chopped pecans or walnuts to the dough for a nice crunch.
• Chocolate Drizzle: Once cooled, drizzle melted white or dark chocolate over the cookies for an elegant finish.
• Mini Version: Make bite-sized cookies perfect for parties or lunchbox treats.
• Spiced Version: Incorporate cardamom or ginger powder into the dough for a subtle spice.

How to Store Leftovers

Store your Pineapple Upside Down Cookies in an airtight container at room temperature for up to 3 days. To keep them fresh longer, refrigerate for up to a week or freeze for up to 3 months. When freezing, separate layers with parchment paper to prevent sticking. Thaw frozen cookies at room temperature before serving for the best texture and flavor.

FAQ

Can I use fresh pineapple instead of canned crushed pineapple?

Absolutely! Fresh pineapple can be used, but make sure to finely crush or chop it and drain any excess juice well to avoid soggy cookies. Fresh pineapple adds a vibrant, natural sweetness that really shines in this recipe.

What can I substitute for maraschino cherries?

If you prefer to skip maraschino cherries or don’t have any on hand, you can use fresh cherries, halved grapes, or even small pieces of dried fruit like cranberries or pineapple chunks. These alternatives will still add a pop of color and sweetness.

Can I make these cookies vegan?

To make vegan Pineapple Upside Down Cookies, replace butter with a plant-based margarine or coconut oil, and use a flax egg (1 tablespoon ground flaxseed mixed with 3 tablespoons water) in place of each egg. Keep in mind the texture and flavor will be slightly different but still delicious.

Why is my pineapple topping not caramelizing properly?

If the pineapple topping isn’t caramelizing, ensure you’re using packed brown sugar and that your oven temperature is accurate. You might also want to bake the cookies a minute or two longer or briefly broil them at the end. Make sure to drain the pineapple well so excess moisture isn’t preventing caramelization.

Conclusion

Pineapple Upside Down Cookie is a delightful fusion of classic dessert flavors wrapped up in a convenient, handheld treat. With its buttery base, sweet and tangy pineapple topping, and that irresistible cherry crown, these cookies are perfect for any occasion. Whether you’re baking for a crowd or craving a tropical-inspired sweet snack, this recipe delivers every time. Try it out and bring a little sunshine to your cookie jar today!

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