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Pineapple Upside Sugar Cookies

Pineapple Upside Sugar Cookies

  • Author: Charlotte
  • Prep Time: 10 minutes
  • Cook Time: 18 minutes
  • Total Time: 30 minutes
  • Yield: 10 cookies 1x
  • Category: Dessert
  • Method: Bake
  • Cuisine: American
  • Diet: Vegetarian

Description

Pineapple Upside Sugar Cookies are a fun, tropical twist on the classic sugar cookie—featuring soft, chewy cookies topped with a slice of sweet pineapple and a maraschino cherry, all caramelized with a touch of brown sugar for that classic upside-down cake flavor in handheld form.


Ingredients

Scale
  • 1 (16.5 oz) roll refrigerated sugar cookie dough
  • 1 can pineapple slices (about 10 rings), drained and patted dry
  • 10 maraschino cherries, stems removed
  • 1/4 cup light brown sugar
  • 2 tablespoons unsalted butter, melted

Instructions

  1. Preheat oven to 350°F (175°C) and lightly grease or line a muffin tin.
  2. In a small bowl, mix melted butter and brown sugar. Place about 1 teaspoon of the mixture into the bottom of each muffin cup.
  3. Place a pineapple slice into each cup and set a maraschino cherry in the center.
  4. Cut sugar cookie dough into 1-inch slices and press one piece over each pineapple slice, covering it completely.
  5. Bake for 15–18 minutes or until cookies are golden brown and set.
  6. Let cool in the tin for 5 minutes, then carefully invert onto a wire rack or tray to release the cookies. Serve warm or at room temperature.

Notes

  • Make sure pineapple slices are well-drained to prevent soggy cookies.
  • You can use homemade sugar cookie dough if preferred.
  • Best served the day they’re baked for maximum caramelized flavor.

Nutrition

  • Serving Size: 1 cookie
  • Calories: 210
  • Sugar: 20g
  • Sodium: 135mg
  • Fat: 9g
  • Saturated Fat: 4g
  • Unsaturated Fat: 3g
  • Trans Fat: 0g
  • Carbohydrates: 30g
  • Fiber: 0.5g
  • Protein: 1g
  • Cholesterol: 10mg

Keywords: pineapple upside down cookies, sugar cookie pineapple dessert, tropical cookie recipe, mini upside-down cake cookies