Pineapple Upside Down Cookies

If you adore the classic flavors of a Pineapple Upside Down Cake but are looking for a portable, bite-sized treat, these Pineapple Upside Down Cookies are your new best friend. Bursting with caramelized sweetness from brown sugar and butter, combined with juicy pineapple and vibrant cherries, these cookies capture that nostalgic tropical flavor in every chewy, tender bite. Whether you’re packing a picnic, prepping for a party, or simply craving a unique cookie that stands out from the usual chocolate chip, this recipe will quickly become a household favorite.

Why This Recipe Is a Must-Try

There’s something magical about the combination of pineapple and cherry paired with the rich, buttery sweetness of brown sugar. These Pineapple Upside Down Cookies bring all those elements together in a delightful way that’s both familiar and fresh. Unlike traditional upside-down cakes, these cookies are easier to handle, faster to bake, and perfect for sharing. Plus, the use of crushed pineapple and cherries gives them a moist texture that sets them apart from your average cookie.

If you love baking, you might also enjoy experimenting with other cookie recipes like the Cake Mix Cookies Recipe, which offers a quick and easy alternative when you’re short on time. But for a burst of tropical flavor that feels both indulgent and fun, these Pineapple Upside Down Cookies are a must-have in your recipe collection.

Ingredients

• 1 cup unsalted butter, softened
• 1 cup brown sugar, packed
• 1 cup granulated sugar
• 2 large eggs
• 2 teaspoons vanilla extract
• 3 cups all-purpose flour
• 1 teaspoon baking soda
• 1/2 teaspoon salt
• 1 cup crushed pineapple, drained
• 1 cup chopped cherries, maraschino or fresh

How To Make Pineapple Upside Down Cookies

Step 1: Prep Your Ingredients

Begin by draining your crushed pineapple thoroughly to avoid excess moisture in your dough. Chop your cherries into small pieces if they aren’t pre-chopped. Preheat your oven to 350°F (175°C) and line baking sheets with parchment paper or silicone baking mats.

Step 2: Cream Butter and Sugars

In a large mixing bowl, use an electric mixer to cream the softened butter with both the brown sugar and granulated sugar. Beat until the mixture is light and fluffy, about 3-4 minutes. This step is crucial to create a tender cookie texture.

Step 3: Add Eggs and Vanilla

Add the eggs one at a time, beating well after each addition. Stir in the vanilla extract. These wet ingredients help bind the dough and add a depth of flavor that enhances the pineapple and cherry notes.

Step 4: Combine Dry Ingredients

In a separate bowl, whisk together the all-purpose flour, baking soda, and salt. Gradually add the dry ingredients to the wet mixture, mixing on low speed until just combined. Avoid overmixing to keep your cookies tender.

Step 5: Fold in Pineapple and Cherries

Gently fold in the drained crushed pineapple and chopped cherries with a spatula. The pineapple adds moisture and a tropical tang, while the cherries provide pops of color and sweetness.

Step 6: Shape and Bake

Using a cookie scoop or tablespoon, drop dough balls about 2 inches apart on the prepared baking sheets. Flatten each slightly with the palm of your hand or the bottom of a glass to encourage even baking. Bake for 12-15 minutes, or until the edges are golden and the centers are set.

Step 7: Cool and Enjoy

Allow the cookies to cool on the baking sheet for 5 minutes before transferring them to a wire rack to cool completely. This helps them set and prevents breakage.

Expert Tips

• Make sure to drain the crushed pineapple very well to prevent your cookie dough from becoming too wet, which can cause spreading.
• For the best texture, use room temperature butter so it creams properly with the sugars.
• Chilling the dough for 30 minutes before baking can help control spreading and intensify flavors.
• If you prefer a stronger caramel flavor reminiscent of classic Pineapple Upside Down Cake, try browning the butter slightly before creaming it with the sugars.
• Use fresh cherries when in season for a more natural flavor, or maraschino cherries for a vivid pop of color and sweetness.

Variations and Customizations

• Add Nuts: Incorporate chopped pecans or walnuts for a crunchy contrast to the soft cookie texture.
• Tropical Twist: Mix in shredded coconut for an extra layer of tropical flavor.
• Spiced Version: Add 1 teaspoon of cinnamon or pumpkin pie spice to the dry ingredients for a warm, cozy twist.
• Glaze It: Drizzle a simple vanilla or pineapple glaze over cooled cookies for added sweetness and presentation.
• Mini Cookie Bites: Make smaller dough balls to create bite-sized cookies perfect for parties or snack trays.

How to Store Leftovers

To keep your Pineapple Upside Down Cookies fresh, store them in an airtight container at room temperature. They’ll stay soft and flavorful for up to 4 days. If you want to keep them longer, freeze the baked cookies in a sealed container for up to 3 months. Thaw at room temperature before serving. Avoid refrigerating as it can dry out the cookies.

FAQ

Can I use canned pineapple for this recipe?

Yes! Just make sure to drain the canned crushed pineapple very well to avoid excess moisture in your cookie dough that could affect the texture.

Are these cookies gluten-free?

This recipe uses all-purpose flour, so it is not gluten-free. However, you can experiment with a gluten-free flour blend that measures cup-for-cup as all-purpose flour, but results may vary slightly.

Can I substitute the cherries with another fruit?

Absolutely! You can use dried cranberries, chopped dried apricots, or even fresh blueberries as alternatives, but keep in mind the flavor profile will change slightly.

How can I make these cookies vegan?

To make this recipe vegan, replace the butter with a plant-based margarine or coconut oil and use a flax or chia egg substitute (1 tablespoon ground flax or chia seeds mixed with 3 tablespoons water per egg).

Conclusion

Pineapple Upside Down Cookies are a delightful twist on a beloved classic dessert. They combine buttery sweetness, tropical pineapple, and bright cherries into an irresistibly chewy cookie that’s perfect for any occasion. Easy to make and full of flavor, these cookies will quickly become a staple in your baking repertoire. Whether you enjoy them fresh from the oven or pack them for a snack on the go, they’re sure to bring a little sunshine to your day. Give this recipe a try and watch how fast they disappear!

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