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Pineapple Upside Sugar Cookies

A tropical twist on classic sugar cookies featuring juicy pineapple and maraschino cherries. These buttery, sweet cookies offer a tender texture and vibrant flavor, perfect for sharing at gatherings or enjoying as a fresh snack.
Prep Time15 minutes
Cook Time12 minutes
Total Time27 minutes
Course: Desserts & Sweets
Cuisine: American
Servings: 24 servings
Calories: 180kcal
Author: AI Generator

Ingredients

  • 1 cup unsalted butter, softened
  • 1 cup granulated sugar
  • 1 large egg
  • 2 teaspoons vanilla extract
  • 2 1/2 cups all-purpose flour
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon salt
  • 1 can pineapple rings, drained and chopped
  • Maraschino cherries, halved
  • 1/2 cup brown sugar
  • 2 tablespoons melted butter

Instructions

  • Preheat oven to 350°F (175°C). Line baking sheets with parchment paper.
  • Cream softened butter and granulated sugar in a bowl until light and fluffy (3-4 minutes).
  • Add egg and vanilla extract; beat until smooth.
  • Whisk together flour, baking powder, and salt in a separate bowl.
  • Gradually mix dry ingredients into the wet mixture until a soft dough forms.
  • Fold in drained pineapple and maraschino cherries.
  • Spoon dough onto prepared baking sheets (about 2 tablespoons per cookie).
  • Bake for 10-12 minutes or until golden.
  • Cool slightly before inverting onto parchment paper to create the "upside" presentation.
  • Serve at room temperature.

Notes

Use non-alcoholic maraschino cherries if concerned about alcohol content.
Chop pineapple to avoid large gaps in the cookies.
Bake in one batch for consistent results.
Store cooled cookies in an airtight container for up to 3 days.
Can substitute fresh pineapple if canned is unavailable (drain thoroughly).