Easy Pineapple Upside Sugar Cookies

Y’all, I had a hankerin’ for something sweet the other day, and the image of pineapple upside-down cake popped into my head. But I wanted something a little different, something, dare I say, a bit more… portable. That’s when the idea for these Pineapple Upside Sugar Cookies struck! Think classic soft sugar cookies, but with a caramelized pineapple “upside” that’s pure Texas sunshine. I’ve made this recipe three times in my kitchen this week alone, and let me tell you, these cookies are disappearin’ faster than bluebonnets in July. If you’re lookin’ for a fun, easy, and totally delicious treat, I promise these cookies will bring a little bit of the Aloha spirit right to your kitchen.

Why This Recipe Works

As a busy momma of two, I know the value of a recipe that delivers big flavor without a ton of fuss. These Pineapple Upside Sugar Cookies are perfect because:

• They’re surprisingly quick: From start to finish, you can have a batch ready in under an hour. Perfect for those last-minute bake sales or when the sweet cravings hit hard.
• Kid-approved: My kiddos absolutely adore the caramelized pineapple. It adds a fun, chewy texture and a burst of tropical flavor that they can’t resist.
• Make-ahead friendly: You can make the sugar cookie dough a day in advance and store it in the fridge, ready to bake whenever you need it.

Ingredients

• For the Pineapple Topping:
  • 1/4 cup (1/2 stick) unsalted butter
  • 1/2 cup packed light brown sugar
  • 1 (20-ounce) can pineapple slices, drained well
  • Maraschino cherries, halved (optional)
• For the Sugar Cookies:
  • 1 cup (2 sticks) unsalted butter, softened
  • 1 cup granulated sugar
  • 2 large eggs
  • 1 teaspoon vanilla extract
  • 3 cups all-purpose flour
  • 1 teaspoon baking powder
  • 1/2 teaspoon baking soda
  • 1/4 teaspoon salt

Ingredient Notes:

• Butter: I always use unsalted butter in my baking recipes so that I can control the amount of salt. Be sure it’s softened but not melted, or your cookies will spread too thin.
• Pineapple: Drain the pineapple slices really well! Excess moisture will make the cookies soggy. Pat them dry with paper towels if you’re feeling extra diligent.
• Flour: Be careful not to over-measure the flour. Spoon it into your measuring cup and level it off with a knife. Too much flour will result in dry, crumbly cookies.
• Vanilla extract: Use pure vanilla extract for the best flavor.

Step-by-Step Instructions

Step 1: Prepare the Pineapple Topping: Preheat your oven to 350°F (175°C). In a 12-cup muffin tin, melt the butter in the oven or microwave. Sprinkle the brown sugar evenly into each muffin cup over the melted butter.

Step 2: Arrange the Pineapple: Place one pineapple slice into each muffin cup. If desired, add a maraschino cherry half in the center of each pineapple ring. This adds a beautiful pop of color and a little extra sweetness!

Step 3: Make the Sugar Cookie Dough: In a large bowl, cream together the softened butter and granulated sugar until light and fluffy. Beat in the eggs one at a time, then stir in the vanilla extract.

Step 4: Combine Dry Ingredients: In a separate bowl, whisk together the flour, baking powder, baking soda, and salt. Gradually add the dry ingredients to the wet ingredients, mixing until just combined. Be careful not to overmix, as this will make the cookies tough.

Step 5: Drop Dough onto Pineapple: Drop rounded tablespoons of sugar cookie dough over the pineapple slices in each muffin cup, gently pressing down to spread evenly. The dough should almost fill each cup, leaving a little room for the cookies to puff up.

Step 6: Bake the Cookies: Bake in the preheated oven for 15-18 minutes, or until the edges are lightly golden brown and the centers are set. After testing this several times, I learned that using a toothpick inserted into the center of a cookie should come out clean is a reliable indication.

Step 7: Cool and Invert: Let the cookies cool in the muffin tin for about 5 minutes. Then, carefully invert the muffin tin onto a wire rack to release the cookies. Be sure to do this while they’re still warm, or the pineapple may stick to the tin.

Step 8: Serve and Enjoy: Let the cookies cool completely on the wire rack before serving. These are best enjoyed fresh, when the cookies are still soft and the pineapple is warm and gooey.

Expert Tips from My Kitchen

• Don’t overbake: Overbaked sugar cookies are dry and crumbly. Keep a close eye on them in the oven and remove them as soon as the edges start to turn golden brown.
• Chill the dough (optional): If you have time, chilling the sugar cookie dough for 30 minutes before baking will help prevent the cookies from spreading too much.
• Use a cookie scoop: A cookie scoop will help you get uniformly sized cookies that bake evenly.
• Get creative with decorations: Feel free to add sprinkles, colored sugar, or a drizzle of icing to the cookies for an extra festive touch.
• Kid-friendly fun: Let the kids help arrange the pineapple slices and cherries in the muffin tin. It’s a great way to get them involved in the baking process!
• Easy cleanup: Spray your muffin tin with non-stick cooking spray for easy cleanup.
• Add spices: Sprinkle a pinch of cinnamon or nutmeg into the sugar cookie dough for a warm, cozy flavor.

Storage & Meal Prep

Storage: Store these Pineapple Upside Sugar Cookies in an airtight container at room temperature for up to 3 days. They’re best enjoyed fresh, but they’ll still be delicious the next day or two.

Meal Prep: You can make the sugar cookie dough up to 2 days in advance and store it in the fridge. Wrap it tightly in plastic wrap to prevent it from drying out. You can also prepare the pineapple topping ahead of time and store it in the fridge for up to 24 hours. Just be sure to drain the pineapple well before using it.

Reheating: To reheat the cookies, warm them in the microwave for a few seconds or in a low oven (200°F) for a few minutes. This will soften them up and make the pineapple extra gooey.

Substitutions & Variations

• Gluten-free: To make these cookies gluten-free, substitute the all-purpose flour with a gluten-free all-purpose flour blend. Be sure to choose a blend that contains xanthan gum, as this will help bind the dough together.
• Dairy-free: You can substitute the butter with a dairy-free butter alternative. Look for one that’s specifically designed for baking.
• Other fruits: While I haven’t personally tried it, you could try using other fruits in place of the pineapple, such as peaches, apples, or pears. Just be sure to adjust the baking time as needed.
• Coconut flakes: Sprinkle some shredded coconut flakes over the pineapple before baking for a tropical twist.

Frequently Asked Questions

Can I make this ahead?

Yes! You can make the sugar cookie dough up to 2 days in advance and store it in the fridge. Wrap it tightly in plastic wrap to prevent it from drying out. You can also prepare the pineapple topping ahead of time and store it in the fridge for up to 24 hours. Just be sure to drain the pineapple well before using it.

How do I know when the cookies are done?

The cookies are done when the edges are lightly golden brown and the centers are set. A toothpick inserted into the center of a cookie should come out clean. Be careful not to overbake them, or they’ll be dry and crumbly.

Can I use fresh pineapple?

Yes, you can use fresh pineapple if you prefer. Just be sure to peel, core, and slice it into rings that are about the same size as the canned pineapple slices. You may need to cook the fresh pineapple slices slightly before using them to soften them up a bit.

Can I freeze these cookies?

Yes, you can freeze these cookies. Let them cool completely, then wrap them individually in plastic wrap and place them in a freezer-safe bag or container. They can be frozen for up to 2 months. Thaw them at room temperature before serving.

Are these cookies kid-friendly?

Absolutely! My kids love these cookies. The caramelized pineapple adds a fun, chewy texture and a burst of tropical flavor that they can’t resist. Plus, they’re easy for little hands to hold and eat.

What if I don’t have a muffin tin?

While a muffin tin is ideal for creating that signature upside-down look, you can still make these cookies on a regular baking sheet. Just form the cookie dough into circles, top with a slice of caramelized pineapple (cooked separately in a skillet with butter and brown sugar), and bake as directed. They won’t be quite as neat, but they’ll still taste amazing!

Serving Suggestions (Optional)

These Pineapple Upside Sugar Cookies are delicious on their own, but here are a few serving suggestions to elevate them even further:

• Serve them warm with a scoop of vanilla ice cream for a decadent dessert.
• Drizzle them with a simple glaze made from powdered sugar and milk.
• Pair them with a cup of coffee or tea for a sweet afternoon treat.

Y’all, these Pineapple Upside Sugar Cookies are more than just a recipe; they’re a little taste of sunshine, baked with love. They’re the kind of treat that brings a smile to everyone’s face and makes even the busiest day feel a little bit brighter. So, gather your ingredients, preheat your oven, and get ready to create some magic in your kitchen. I just know your family is gonna love them! Be sure to come back and let me know how they turned out in the comments below, and don’t forget to sign up for my newsletter for more delicious recipes delivered straight to your inbox! I can’t wait to hear about your baking adventures with these Pineapple Upside Sugar Cookies!

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