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Pineapple Upside Down Sugar Cookies: A Tropical Delight!

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These pineapple upside down sugar cookies feature caramelized pineapple atop a tender, sugar-kissed cookie, balancing acidity with warmth.

  • Total Time: 30 minutes
  • Yield: 24 cookies 1x

Ingredients

Scale
  • 1 cup Unsalted Butter (softened)
  • 1 cup Granulated Sugar
  • 1 large Egg (substitutable with a chia egg for a vegan option)
  • 1 teaspoon Vanilla Extract (can substitute with almond extract)
  • 2 cups All-Purpose Flour (can use gluten-free blend)
  • 1 teaspoon Baking Soda (ensure fresh)
  • 1 teaspoon Salt
  • 1 can Canned Pineapple Rings (or fresh pineapple, dried well)
  • 1 tablespoon Additional Sugar for Sprinkling (optional)

Instructions

  1. Preheat the oven to 350°F (175°C) and line a baking sheet with parchment paper.
  2. Cream softened butter and granulated sugar until pale and slightly aerated, about two to three minutes.
  3. Beat in the egg and vanilla extract until smooth and fragrant.
  4. Whisk together flour, baking soda, and salt; fold into the butter mixture until just combined. Chill the dough for 15 to 30 minutes for cleaner edges.
  5. Divide dough into uniform balls, flatten slightly, and place on the prepared sheet, allowing two inches between each.
  6. Drain pineapple rings thoroughly; if using fresh, pat dry and caramelize briefly in a hot skillet to remove excess moisture. Center a ring atop each flattened dough disk and press gently.
  7. Sprinkle additional sugar on the ring for a fine crunch if desired. Bake for 10–12 minutes, or until edges turn light golden and centers hold form.
  8. Remove from oven and let cool on the sheet for five minutes to let the juices settle, then transfer to a rack to finish cooling.

Notes

Chill the dough briefly to prevent over-spreading and to keep the pineapple ring centered during bake. Watch the first batch closely, as ovens vary.

  • Author: Sam Razal
  • Prep Time: 15 minutes
  • Cook Time: 12 minutes
  • Category: Dessert
  • Method: Baking
  • Cuisine: American
  • Diet: Vegetarian

Nutrition

  • Serving Size: 1 cookie
  • Calories: 160
  • Sugar: 10g
  • Sodium: 150mg
  • Fat: 8g
  • Saturated Fat: 4g
  • Unsaturated Fat: 3g
  • Trans Fat: 0g
  • Carbohydrates: 20g
  • Fiber: 1g
  • Protein: 2g
  • Cholesterol: 20mg