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Pineapple Upside Down Sugar Cookies


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  • Author: veronica
  • Total Time: 60 minutes
  • Yield: 24 cookies 1x
  • Diet: Vegetarian

Description

Bright, syrupy pineapple rings caramelize on top of buttery sugar-cookie dough for a delightful summer treat.


Ingredients

Scale
  • 300 g (2 1/2 cups) all-purpose flour
  • 6 g (1 1/2 tsp) baking powder
  • 5 g (1 tsp) kosher salt
  • 226 g (1 cup) unsalted butter, softened
  • 200 g (1 cup) granulated sugar
  • 1 large egg (50 g)
  • 10 ml (2 tsp) pure vanilla extract
  • 120 g (1/2 cup) crushed pineapple, drained
  • 60 ml (1/4 cup) reserved crushed pineapple juice
  • Pineapple rings, canned, drained and patted dry, about 12
  • 60 g (1/3 cup packed) brown sugar (for topping)
  • 1 tsp lemon zest (optional)
  • 30 g (1/4 cup) chopped toasted macadamia nuts or macerated cherries (optional)

Instructions

  1. Make the Pineapple Caramel: In a small saucepan, combine 60 g (1/3 cup) brown sugar and 30 g (2 tbsp) unsalted butter over medium heat until syrupy, about 2–3 minutes.
  2. Prepare Dry Ingredients: Whisk together flour, baking powder, and kosher salt in a medium bowl; set aside.
  3. Cream Butter and Sugar: In a mixer, cream butter and granulated sugar on medium speed for 2–3 minutes until pale and fluffy.
  4. Combine Wet and Dry: Add half the dry ingredients to the butter mixture and mix on low until just combined; then add crushed pineapple and remaining dry ingredients.
  5. Chill the Dough: Turn dough onto plastic wrap, press into a disk, and chill for 20–30 minutes.
  6. Shape Cookies and Add Pineapple: Preheat oven to 180°C (350°F), roll dough to 6 mm thickness, cut rounds, and top each with pineapple caramel and a pineapple slice.
  7. Bake: Bake for 10–12 minutes until edges are golden and centers are set.
  8. Finish and Store: Let cool on the pan for 5 minutes, then transfer to a cooling rack.

Notes

Chill dough for better shape and texture. Store cookies in an airtight container for up to 3 days.

  • Prep Time: 20 minutes
  • Cook Time: 12 minutes
  • Category: Dessert
  • Method: Baking
  • Cuisine: American

Nutrition

  • Serving Size: 1 cookie
  • Calories: 160
  • Sugar: 11g
  • Sodium: 95mg
  • Fat: 8g
  • Saturated Fat: 4.5g
  • Unsaturated Fat: 3.5g
  • Trans Fat: 0g
  • Carbohydrates: 20g
  • Fiber: 0.7g
  • Protein: 2g
  • Cholesterol: 25mg