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Pineapple Upside Sugar Cookies

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  • Author: Sue
  • Prep Time: 15 minutes
  • Cook Time: 15 minutes
  • Total Time: 30 minutes
  • Yield: 12 cookies
  • Category: Dessert
  • Method: Baking
  • Cuisine: American
  • Diet: Vegetarian

Description

These pineapple upside sugar cookies combine the sweet, buttery flavor of sugar cookies with caramelized pineapple and cherry for a fun, mini twist on the classic upside-down cake.


Ingredients

  • 1 batch sugar cookie dough (homemade or store-bought)
  • 12 pineapple rings (canned, drained, and patted dry)
  • 12 maraschino cherries
  • 12 tsp brown sugar
  • 12 tsp unsalted butter, melted

Instructions

  1. Preheat the oven to 350°F (175°C) and spray a muffin tin with non-stick spray.
  2. Add 1 teaspoon of melted butter and 1 teaspoon of brown sugar to each muffin cup.
  3. Place a pineapple ring into each muffin cup, trimming as needed to fit.
  4. Add a maraschino cherry in the center of each pineapple ring.
  5. Press a ball of sugar cookie dough on top of the pineapple and cherry, flattening slightly.
  6. Bake for 12–15 minutes, until the cookies are golden and set.
  7. Let cookies cool in the pan for 5 minutes, then carefully flip them onto a baking sheet to cool completely.

Notes

  • Swap sugar cookie dough with shortbread dough for a richer taste.
  • Add shredded coconut to the brown sugar layer for a tropical twist.
  • Use mini muffin tins with pineapple tidbits for bite-sized cookies.
  • Store in an airtight container for up to 3 days at room temperature or refrigerate up to 5 days.
  • Reheat in the microwave for 10–15 seconds to refresh the flavor and texture.

Nutrition

  • Serving Size: 1 cookie
  • Calories: 180
  • Sugar: 18 g
  • Sodium: 95 mg
  • Fat: 8 g
  • Saturated Fat: 5 g
  • Unsaturated Fat: 2 g
  • Trans Fat: 0 g
  • Carbohydrates: 25 g
  • Fiber: 0.5 g
  • Protein: 1 g
  • Cholesterol: 15 mg