Print
clock clock iconcutlery cutlery iconflag flag iconfolder folder iconinstagram instagram iconpinterest pinterest iconfacebook facebook iconprint print iconsquares squares iconheart heart iconheart solid heart solid icon

Pineapple Upside Down Sugar Cookies Recipe

5 Stars 4 Stars 3 Stars 2 Stars 1 Star 4.1 from 87 reviews
  • Author: admin
  • Prep Time: 10 minutes
  • Cook Time: 15 minutes
  • Total Time: 25 minutes
  • Yield: 12 cookies
  • Category: Dessert
  • Method: Baking
  • Cuisine: American
  • Diet: Vegetarian

Description

These Pineapple Upside Sugar Cookies combine the tropical flavors of pineapple and maraschino cherries with classic sugar cookie dough for a fun and fruity dessert. Featuring a gooey brown sugar and butter base topped with juicy pineapple and cherries, these easy-to-make cookies are baked in a muffin tin and inverted for a stunning presentation perfect for parties or everyday treats.


Ingredients

Scale

Cookie Base

  • 1 roll (16.5 ounces) refrigerated sugar cookie dough

Topping

  • 1/3 cup brown sugar
  • 2 tablespoons unsalted butter, melted
  • 12 maraschino cherries, halved
  • 1/2 cup crushed pineapple, well drained


Instructions

  1. Prepare Oven and Pan: Preheat the oven to 350°F and lightly grease a standard 12-cup muffin tin to prevent sticking.
  2. Mix Butter and Sugar: In a small bowl, combine the melted butter and brown sugar until well blended, creating a sweet base for the cookies.
  3. Add Toppings to Muffin Cups: Spoon about 1 teaspoon of the brown sugar and butter mixture into the bottom of each muffin cup. Place half a maraschino cherry in the center of each, then add approximately 2 teaspoons of well-drained crushed pineapple around the cherry for a tropical flavor burst.
  4. Prepare Cookie Dough: Cut the sugar cookie dough into 12 equal portions, slightly flatten each to create a disc that will fit atop the fruit mixture in each muffin cup.
  5. Assemble Cookies: Place each flattened dough piece over the pineapple and cherry mixture in the muffin cups, covering the fruit base completely.
  6. Bake: Bake for 12 to 15 minutes, or until the cookie edges are golden and the cookie is cooked through.
  7. Cool and Invert: Let the cookies cool in the pan for about 5 minutes, then run a knife around the edges to loosen them. Carefully invert the muffin tin onto a wire rack or tray to release the upside-down pineapple topping and reveal the caramelized brown sugar layer.
  8. Serve: Serve the cookies warm or at room temperature for the best flavor and texture experience.

Notes

  • Drain the pineapple thoroughly to avoid soggy cookie bottoms.
  • These cookies are perfect for parties or as a fun tropical twist on classic sugar cookies.
  • For easier removal, greasing the muffin tin well or using nonstick spray is recommended.
  • Use a sharp knife to loosen edges carefully before inverting to maintain cookie shape.