Pineapple Upside Down Sugar Cookies That Delight Every Bite

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Pineapple Upside Down Sugar Cookies That Delight Every Bite

⏱ Prep Time: 20 minutes
⏱ Cook Time: 18 minutes
⏱ Total Time: 38 minutes
🍽 Servings: 24 cookies
🥗 Diet: Vegetarian

✨ Description

These Pineapple Upside Down Sugar Cookies combine the classic buttery softness of sugar cookies with the sweet, caramelized flavor of pineapple. Inspired by the nostalgic upside-down cake, each cookie is topped with a golden pineapple ring and a glossy brown sugar glaze that melts into every bite. Perfect for parties, holidays, or whenever you want a unique homemade treat that stands out!

🧾 Ingredients

🍪 For the Sugar Cookie Dough:

  • 2 ¾ cups all-purpose flour
  • 1 teaspoon baking soda
  • ½ teaspoon baking powder
  • 1 cup unsalted butter (softened)
  • 1 ½ cups granulated sugar
  • 1 egg
  • 1 teaspoon vanilla extract
  • 2 tablespoons milk

For the Topping:

  • 1 can pineapple rings (drained well)
  • 24 maraschino cherries 🍒
  • ½ cup brown sugar
  • ¼ cup melted butter

🧰 Equipment:

  • Baking sheet
  • Parchment paper
  • Mixing bowls
  • Hand or stand mixer
  • Cookie cutter or glass
  • Spoon

👩‍🍳 Step-by-Step Instructions

1️⃣ Prepare the Dough

In a bowl, whisk together flour, baking soda, and baking powder.
In another large bowl, beat the softened butter and sugar until light and fluffy.
Add the egg, vanilla extract, and milk, mixing until smooth.
Gradually add the dry ingredients into the wet mixture and mix until a soft dough forms.

👉 Cover and chill the dough for 15–20 minutes (this makes it easier to handle).

2️⃣ Prepare the Pineapple Topping

Preheat your oven to 180°C (350°F).
Line a baking tray with parchment paper.

In a small bowl:

  • Mix melted butter with brown sugar

Spoon a small amount of this mixture onto the baking sheet for each cookie.
Place a small piece of pineapple (cut from rings) on top.
Add a cherry in the center 🍒

3️⃣ Shape the Cookies

Take the chilled dough and roll it into small balls.
Flatten slightly and place each piece on top of the pineapple topping.

👉 Make sure the dough covers the fruit slightly but not completely.

4️⃣ Bake

Bake in the preheated oven for 15–18 minutes, or until edges are lightly golden.

5️⃣ Flip & Cool

Let cookies cool for 5 minutes after baking.
Carefully flip each cookie so the pineapple side is on top (like upside-down cake).

👉 Let them cool completely before serving.

😍 Final Result

Soft, buttery cookies with a caramelized pineapple topping and a juicy cherry center. Sweet, slightly tangy, and absolutely irresistible!

💡 Pro Tips:

  • Pat pineapple dry to avoid soggy cookies
  • Use fresh pineapple for a stronger flavor
  • Don’t overbake to keep cookies soft
  • Chill dough for best texture

🔥 Serving Ideas:

  • Serve warm with tea or coffee ☕
  • Add a scoop of vanilla ice cream 🍨
  • Perfect for parties & dessert tables

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