Pineapple Upside Sugar Cookies Recipe

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Cozy Pineapple Upside Sugar Cookies Recipe, Made Simple

When I first discovered this Pineapple Upside Sugar Cookies Recipe, it instantly became my go-to for weekend baking. There’s something wonderfully joyful about the way those golden pineapple circles crown the buttery, crisp cookies. It’s like sunshine on your plate—a lively pop of tropical sweetness mingling with classic sugar cookie comfort.

You’ll find these cookies perfect for sharing over a cup of tea or packing into a picnic basket. The lightly caramelized edges and the tender crumb invite you to slow down and savor each bite. I love how easy they are, yet they always impress with their fresh, bright flavors.

Let me walk you through everything you need to know so your Pineapple Upside Sugar Cookies come out perfectly every time. From ingredient insights to tips on getting that perfect balance of soft and crisp, I’ve got you covered.

Ingredient Lowdown

• Unsalted butter: Provides richness and tender crumb. Make sure it’s softened but not melted for the best creaming.
• Granulated sugar: Gives that classic sugary crispness and sweet balance.
• Egg: Acts as a binder and adds moisture for soft, chewy texture.
• Vanilla extract: Infuses warm aroma and depth.
• All-purpose flour: The structure backbone of these cookies—if you want a lighter cookie, try a mix with cake flour.
• Baking soda: Helps with gentle rise and tender crumb.
• Salt: Balances sweetness and enhances the flavors.
• Canned pineapple rings: The star! Well-drained and patted dry to avoid soggy cookies.
• Additional sugar: Sprinkled on top for that toasty crunch and sparkle.

Set Up for Success

Before you dive in, preheat your oven to a steady 350°F (175°C) and line your baking sheets with parchment paper—this ensures your cookies bake evenly and release easily. Get all your ingredients measured out and ready to go; it keeps the rhythm smooth, especially when the butter and sugar need that perfect fluffy cream.

Step-by-Step: Pineapple Upside Sugar Cookies Recipe

1. Preheat your oven to 350°F (175°C) and line baking sheets with parchment paper. I find parchment essential to prevent sticking and to help the cookies bake evenly without hot spots.
2. Cream the softened butter and granulated sugar together in a large bowl using a hand mixer or stand mixer. Beat until it’s light and fluffy—usually about 3-4 minutes. This aeration is key for a tender, melt-in-your-mouth texture.
3. Beat in the egg and vanilla extract until well combined. The dough will start to come together and smell wonderfully fragrant.
4. In a separate bowl, whisk together the flour, baking soda, and salt. Gradually add this dry mix to the butter mixture. Stir just until a soft dough forms—you’ll want it soft but not sticky.
5. Roll the dough into 1½ tablespoon-sized balls. I like to gently flatten each ball so they bake evenly; too thick and the middle might stay soft, too thin and they’ll crisp up quickly.
6. Place dough disks on the prepared baking sheet spaced about 2 inches apart to give them room to spread.
7. Top each dough disk with a well-drained, patted-dry pineapple ring. Press gently to make sure it sticks, but don’t push so hard that the dough squeezes out the sides.
8. Sprinkle some sugar on top of each pineapple ring—this adds sparkle and caramelizes slightly in the oven for an irresistible crunch.
9. Bake for 12–14 minutes or until the edges are a warm golden brown and you catch that gentle aroma of toasty butter and sweet pineapple.
10. Let cool on the baking sheet for 5 minutes, then transfer to a wire rack. This resting time helps the cookies firm up without losing softness inside.

Flavor Twists for Pineapple Upside Sugar Cookies Recipe

• Add a sprinkle of toasted coconut flakes on the pineapple before baking to boost tropical vibes.
• Mix in a teaspoon of finely grated ginger to the dough for a warm, spicy hint.
• Swap pineapple rings for thin apple slices and a dash of cinnamon for autumnal flavor.
• For a boozy touch, brush pineapple rings with a little rum or brandy before topping cookies.
• Roll the dough balls in cinnamon sugar before pressing pineapple on top for extra crunch and spice.

Storage & Make-Ahead Tips

• Store cooled cookies in an airtight container at room temperature for up to 4 days; they stay tender but crisp at the edges.
• Freeze baked cookies in a single layer on a baking sheet, then transfer to freezer bags for up to 3 months.
• To reheat, warm cookies gently in a low oven (about 300°F) for 5-7 minutes to bring back that fresh-baked feel.
• You can also freeze the cookie dough balls before baking. Thaw in the fridge overnight for fuss-free baking later.

Pineapple Upside Sugar Cookies Recipe FAQs

• Can I use fresh pineapple instead of canned? Fresh pineapple works but be sure to slice very thin pieces and dry them thoroughly to avoid soggy cookies.
• What if I don’t have baking soda? Baking soda helps achieve a tender crumb with some rise, but you can substitute with baking powder—use about 1.5 teaspoons instead.
• Why do my pineapple rings have liquid after draining? Canned pineapple can retain juice. Patting dry with paper towels is crucial to prevent cookies from spreading too much or getting soggy.
• Are these cookies soft or crispy? You’ll get a lovely balance—the edges turn toasty and crisp while the centers stay tender with a slight chew.
• Can I make these cookies gluten-free? You can substitute all-purpose flour with a gluten-free baking blend, but be sure it contains xanthan gum or add a little to help with texture.

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