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Pineapple Upside-Down Cookies A Fun Twist on a Classic Dessert

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Experience the magic of Pineapple Upside-Down Cookies! Golden caramel, juicy pineapple, and a sweet cherry crown each buttery cookie.

Ingredients

  • All-purpose flour: 1 ¾ cups
  • Unsalted butter: ¾ cup, divided (½ cup softened, ¼ cup melted)
  • Granulated sugar: ½ cup
  • Light brown sugar: ¼ cup
  • Large egg: 1
  • alcohol-free vanilla extract: 1 teaspoon
  • Baking powder: ½ teaspoon
  • Canned crushed pineapple & Maraschino cherries: ½ cup well-drained crushed pineapple, 6-8 maraschino cherries (halved)

Instructions

  1. Step 1: Preheat your oven to 375°F (190°C). Lightly grease or line a 12-cup standard muffin tin. In the bottom of each muffin cup, add about ½ teaspoon of the melted butter, followed by a sprinkle of light brown sugar (about 1 teaspoon). Place a halved maraschino cherry in the center of the brown sugar, then arrange a small amount of the well-drained crushed pineapple around the cherry.
  2. Step 2: In a large bowl, cream together the softened ½ cup butter and granulated sugar until the mixture is light and fluffy. Beat in the large egg and vanilla powder until they are well combined, scraping down the sides of the bowl as needed.
  3. Step 3: In a separate medium bowl, whisk together the all-purpose flour and baking powder. Gradually add these dry ingredients to the wet mixture, mixing on low speed until just combined to form a soft cookie dough. Be careful not to overmix.
  4. Step 4: Take about 1-2 tablespoons of cookie dough for each cookie and gently place it on top of the pineapple and cherry mixture in each muffin cup. Lightly press the dough down to cover the topping completely, ensuring it fills the cup.
  5. Step 5: Bake for 12-15 minutes, or until the edges of the cookies are lightly golden brown. Let the cookies cool in the muffin tin for 5-7 minutes before carefully inverting them onto a wire rack to cool completely, revealing the caramelized pineapple and cherry topping.

Notes

  • Store these delightful cookies in an airtight container at room temperature for up to 3 days to maintain their delicious texture.
  • For a delightful treat, gently warm these cookies in the microwave for 10-15 seconds to bring back their cozy, just-baked softness.
  • Elevate these fun cookies by serving them slightly warm with a scoop of vanilla ice cream or a dollop of fresh whipped cream for a truly decadent treat.
  • For that perfect 'upside-down' reveal, be patient! Let the cookies cool in the muffin tin for the full 5-7 minutes; this allows the caramelized topping to set beautifully and prevents sticking.

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