Pineapple Upside Sugar Cookies

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🍍 Pineapple Upside Sugar Cookies

All the nostalgic flavor of pineapple upside-down cake — reimagined as soft, buttery sugar cookies with caramelized pineapple goodness.

If you love classic desserts with a playful twist, these Pineapple Upside Sugar Cookies are guaranteed to steal the spotlight. Inspired by the beloved pineapple upside-down cake, these cookies combine tender sugar-cookie dough with sweet, caramelized pineapple and a hint of vanilla for a tropical-meets-comfort flavor profile.

They’re soft in the center, lightly crisp around the edges, and bursting with fruity sweetness in every bite. Perfect for holidays, potlucks, bake sales, or just because — these cookies feel special while still being easy enough for everyday baking.

⭐ Why You’ll Love These Cookies

  • Inspired by a classic, nostalgic dessert

  • Soft, buttery sugar cookie base

  • Sweet pineapple flavor with caramel notes

  • Easy to make with simple ingredients

  • Eye-catching and bakery-worthy

🛒 Ingredients

For the Cookie Dough

  • 1 cup unsalted butter, softened

  • 1 cup granulated sugar

  • 1 large egg

  • 1 teaspoon vanilla extract

  • 2 ½ cups all-purpose flour

  • ½ teaspoon baking powder

  • ¼ teaspoon baking soda

  • ¼ teaspoon salt

For the Pineapple Topping

  • 1 cup crushed pineapple, very well drained

  • ¼ cup brown sugar

  • 2 tablespoons melted butter

Optional Garnish

  • Maraschino cherry pieces

  • Powdered sugar for dusting

🔪 Prep Tips for Best Results

  • Drain pineapple thoroughly to avoid soggy cookies

  • Use room-temperature butter for proper creaming

  • Chill dough briefly if it feels too soft

  • Press pineapple gently so it caramelizes without spreading

🍪 Step-by-Step Instructions

Step 1: Prepare the Pineapple Topping

In a small bowl, mix crushed pineapple with brown sugar and melted butter.

Set aside while preparing the cookie dough.

Step 2: Make the Cookie Dough

In a large mixing bowl, cream the softened butter and granulated sugar until light and fluffy (about 2–3 minutes).

Add the egg and vanilla extract and mix until fully combined.

In a separate bowl, whisk together flour, baking powder, baking soda, and salt. Gradually add dry ingredients to the wet mixture, mixing just until a soft dough forms.

Step 3: Shape the Cookies

Preheat oven to 350°F (175°C) and line baking sheets with parchment paper.

Scoop about 1½ tablespoons of dough and roll into balls. Place on baking sheets, spacing 2 inches apart.

Use your thumb or the back of a spoon to gently press an indentation in the center of each cookie.

Step 4: Add Pineapple

Spoon a small amount of pineapple mixture into the center of each cookie.

Optional: add a small cherry piece on top for a classic pineapple upside-down cake look.

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