Pineapple Upside Sugar Cookies

If you adore the buttery charm of sugar cookies and crave the sweet-tart zing of pineapple, these Pineapple Upside Sugar Cookies are calling your name. A soft, chewy sugar cookie meets caramelized pineapple in every bite—bringing a tropical twist to classic comfort. Whether you’re baking for a gathering or just a cozy night in, these treats are guaranteed to impress.

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💛 What Makes Them Special

• Tropical Brightness: Juicy pineapple delivers a burst of island flavor.
• Perfect Texture: Soft, tender sugar cookies with a golden edge.
• Quick Bake: Done in under 30 minutes—perfect for last-minute cravings.
• Fun to Customize: Add-ins like coconut, nuts, or a sweet glaze make them uniquely yours.

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🛒 Ingredients (Yields 12–16 Cookies)

Part	Ingredient	Amount	Notes
Topping	Pineapple (fresh or canned)	1, thinly sliced	Canned rings work if short on time
	Melted unsalted butter	2 tablespoons
	Brown sugar	2 tablespoons
	Ground cinnamon (optional)	¼ teaspoon	Adds warm spice
Cookie Dough	Softened unsalted butter	1 cup
	Granulated sugar	1 cup
	Large egg	1
	Pure vanilla extract	1 teaspoon
	All-purpose flour	2¼ cups
	Baking powder	1 teaspoon
	Salt	¼ teaspoon

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👩‍🍳 Step-by-Step Instructions

1. Preheat Oven
Set to 350°F (175°C). Line a baking sheet with parchment or lightly grease it.

2. Prepare the Pineapple Topping

• Brush each pineapple slice with melted butter.
• Sprinkle with brown sugar and cinnamon (if using).
• Lay flat on the prepared baking sheet.

3. Make the Sugar Cookie Dough

• Cream butter and sugar together until fluffy.
• Add the egg and vanilla; mix until smooth.
• In another bowl, whisk flour, baking powder, and salt.
• Slowly add dry ingredients to the wet mixture and mix until combined.

4. Assemble Cookies

• Scoop 1–2 tablespoons of dough and flatten into a round.
• Gently place each dough disc on top of a pineapple slice, pressing lightly to cover.

5. Bake

• Bake for 12–15 minutes until edges are just golden.
• Let cool for 2–3 minutes on the baking sheet.

6. Flip & Finish

• Carefully flip each cookie so the pineapple is on top.
• Optional: Drizzle with a powdered sugar glaze or sprinkle with coconut for extra flair.

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🌟 Baking Tips

• Fresh is Best: Use fresh pineapple for more natural caramelization.
• Add Some Crunch: Chopped pecans or macadamia nuts pair beautifully.
• Flavor Boost: Swap brown sugar with coconut sugar for deeper sweetness.
• Storage: Store in an airtight container at room temp for 2 days or refrigerate for up to 5. Let return to room temperature before serving.