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Pineapple upside down sugar cookies with caramelized tops

Pineapple Upside Down Sugar Cookies

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These pineapple upside down sugar cookies are gooey, fruity, and golden-topped with caramelized pineapple and cherries. They’re like a mini cake with a sugar cookie twist!

  • Total Time: 25 mins
  • Yield: 12 cookies 1x

Ingredients

Scale

1/2 cup unsalted butter (for topping)

1/2 cup light brown sugar

1 cup pineapple tidbits or chunks, well drained

12 maraschino cherries, halved

1/2 cup unsalted butter (for dough)

3/4 cup granulated sugar

1 large egg

1 tsp vanilla extract

1 1/2 cups all-purpose flour

1/2 tsp baking soda

1/4 tsp salt

Instructions

1. Preheat oven to 350°F. Grease mini muffin pan generously.

2. In each cavity, add 1/2 tsp butter, 1 tsp brown sugar, 3–4 pineapple pieces, and half a cherry.

3. Cream butter and sugar for the dough. Add egg and vanilla, mix until smooth.

4. In a separate bowl, whisk flour, baking soda, and salt.

5. Combine dry and wet ingredients until a dough forms.

6. Scoop small dough balls and press them over the fruit in the muffin tin.

7. Bake for 12–15 minutes until edges are golden.

8. Let rest for 5 minutes, then carefully flip onto a tray.

9. Serve warm or cool, store in airtight container.

Notes

Make sure fruit is well-drained to avoid soggy bottoms.

Use paper towels to dry pineapple and cherries before layering.

To reheat, microwave cookies for 8–10 seconds.

  • Author: Chef Saly
  • Prep Time: 10 mins
  • Cook Time: 15 mins
  • Category: Dessert
  • Method: Baking
  • Cuisine: American
  • Diet: Vegetarian

Nutrition

  • Serving Size: 1 cookie
  • Calories: 165
  • Sugar: 18g
  • Sodium: 70mg
  • Fat: 8g
  • Saturated Fat: 5g
  • Unsaturated Fat: 2g
  • Trans Fat: 0g
  • Carbohydrates: 23g
  • Fiber: 0g
  • Protein: 1g
  • Cholesterol: 25mg