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Pineapple Upside Down Cookies

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A delightful single-serve treat that transforms the classic pineapple upside-down cake into cookies, featuring caramelized pineapple and cherries topped with a soft cookie dough.

Ingredients

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  • 1 cup sugar
  • 1/2 cup butter, softened
  • 1 egg
  • 2 cups all-purpose flour
  • 1 teaspoon baking powder
  • 1/2 teaspoon salt
  • 1/2 cup brown sugar for sprinkling
  • 1 can pineapple slices, drained
  • Maraschino cherries for centers
  • 1/4 cup brown sugar for glaze
  • 1 tablespoon milk

Instructions

  1. Preheat the oven to 350°F (175°C).
  2. Cream together the sugar and softened butter until smooth.
  3. Beat in the egg until fully incorporated.
  4. Whisk together the flour, baking powder, and salt in another bowl.
  5. Gradually add the dry mix to the creamed mixture.
  6. Place a drained pineapple slice in each muffin cup, press a maraschino cherry into the center, and sprinkle brown sugar over the fruit.
  7. Drop spoonfuls of cookie dough over each pineapple slice.
  8. Bake for 15 to 20 minutes or until golden brown.
  9. Allow cookies to cool slightly before inverting onto a wire rack.
  10. Mix the brown sugar with the milk until smooth and drizzle over the cookies.

Notes

Store cooled cookies in an airtight container in the refrigerator for up to 4 days. For longer storage, freeze individual cookies for up to 2 months.

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