Pineapple Upside Sugar Cookies

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Pineapple Upside Sugar Cookies are a delightful twist on the classic pineapple upside-down cake. These cookies combine a soft, tender sugar cookie base with caramelized pineapple and maraschino cherries for a tropical treat. Each bite is a burst of buttery, fruity goodness, making them perfect for parties, gatherings, or just satisfying a sweet tooth.

Ingredients

For the Cookies:

• 1 cup butter (room temperature)
• 1 ½ cups granulated sugar
• 2 eggs
• 2 teaspoons vanilla extract
• ½ cup sour cream
• 3 cups all-purpose flour
• 1 teaspoon baking powder
• 1 teaspoon cornstarch
• ½ teaspoon salt

For the Toppings:

• 13 canned pineapple slices
• 13 maraschino cherries
• ½ cup melted butter
• 1 cup packed light brown sugar

Directions

Preheat the Oven and Prep the Pan

1. Preheat your oven to 350°F.
2. Grease a mini round cake pan (like a USA Pan) or a similar pan and set aside.

Mix the Cookie Dough

1. In a large mixing bowl, cream the butter and sugar together until light and fluffy.
2. Add the eggs, vanilla extract, and sour cream, mixing until well combined.
3. Slowly add in the flour, baking powder, cornstarch, and salt, mixing just until the dough comes together. Set the dough aside.

Prepare the Brown Sugar Glaze

1. In a separate bowl, stir together the melted butter and brown sugar until smooth.

Assemble the Cookies

1. Drop about 1 tablespoon of the brown sugar mixture into each cavity of the pan, spreading it evenly.
2. Place a pineapple slice on top of the brown sugar mixture and position a maraschino cherry in the center of the pineapple.
3. Scoop out about 3 tablespoons of the cookie dough and place it on top of each pineapple slice. Use a spatula to gently flatten the dough to cover the pineapple.

Bake and Cool

1. Bake for about 25 minutes, or until the edges of the cookies are golden brown and the brown sugar is bubbling around the edges.
2. Let the cookies cool in the pan for 10 minutes, then carefully turn them out onto a surface covered with wax paper. If any pineapple sticks, gently reposition it on the cookie.
3. Allow the cookies to cool completely before enjoying.

Servings and Timing

This recipe makes 13 cookies. Prep time is about 20 minutes, and baking time is 25 minutes. Allow an additional 10 minutes for cooling.

Variations

• Coconut Lovers: Add shredded coconut to the cookie dough or sprinkle it on top of the pineapple before baking for an extra tropical twist.
• Pineapple Substitute: For a different flavor, swap the pineapple with canned peach or apricot slices.
• Spiced Version: Add a pinch of cinnamon and nutmeg to the dough for a warm, spiced flavor that complements the pineapple.

Storage and Reheating

• Storage: Store the cookies in an airtight container at room temperature for up to 3 days. Refrigeration may extend their freshness for an additional 1-2 days, but they’re best enjoyed within the first few days.
• Reheating: To bring back their soft, warm texture, microwave individual cookies for about 10-15 seconds before serving.

10 Frequently Asked Questions

1. Can I use fresh pineapple instead of canned?
   Yes, fresh pineapple can be used, but make sure to slice it thinly to avoid excess moisture.
2. Can I freeze these cookies?
   Yes, these cookies freeze well. Wrap them tightly and freeze for up to 2 months. Thaw at room temperature before serving.
3. What’s the best substitute for sour cream?
   You can use Greek yogurt or buttermilk as a substitute for sour cream.
4. Can I make these cookies ahead of time?
   Yes, you can prepare the cookie dough a day ahead and store it in the refrigerator. Bake them fresh when ready.
5. Can I use a different type of sugar for the glaze?
   Light brown sugar is best for caramelizing, but you can try dark brown sugar for a deeper flavor.
6. Why did my pineapple stick to the pan?
   Make sure the pan is well-greased, and allow the cookies to cool for 10 minutes before turning them out.
7. Can I make this recipe gluten-free?
   Yes, substitute the all-purpose flour with a gluten-free flour blend designed for baking.
8. What if I don’t have a mini round cake pan?
   You can use a muffin tin instead, adjusting the size of the pineapple slices to fit.
9. How do I know when the cookies are done?
   The cookies are ready when the edges are golden brown and the brown sugar glaze is bubbling.
10. Can I use salted butter?
    Yes, but reduce the salt in the dough to avoid overly salty cookies.

Conclusion

Pineapple Upside Sugar Cookies are a tropical treat that’s easy to make and perfect for sharing. The soft, buttery cookie paired with caramelized pineapple and cherries is a delightful combination that’s sure to impress. Whether you enjoy them fresh from the oven or as a next-day snack, these cookies are a crowd-pleaser with a fruity twist.