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Pineapple Upside Down Cookies

Pineapple Upside Down Cookies


  • Total Time: 32 minute
  • Yield: 12 cookies 1x
  • Diet: Vegetarian

Description

These Pineapple Upside Down Cookies are a fun twist on the classic cake—mini versions of the beloved dessert, baked into soft, buttery cookies. Each cookie features a caramelized pineapple ring and cherry on top, making them perfect for parties, holidays, or just a tropical treat at home.


Ingredients

Scale

Topping:

  • 1/4 cup unsalted butter, melted

  • 1/2 cup brown sugar, packed

  • 12 pineapple rings (canned, drained and patted dry)

  • 12 maraschino cherries

Cookie Dough:

  • 1/2 cup unsalted butter, softened

  • 1/2 cup granulated sugar

  • 1/4 cup brown sugar

  • 1 large egg

  • 1 tsp vanilla extract

  • 1 1/2 cups all-purpose flour

  • 1/2 tsp baking powder

  • 1/4 tsp baking soda

  • 1/4 tsp salt


Instructions

  1. Preheat oven to 350°F (175°C). Grease a standard muffin tin or line with silicone liners.

  2. Prepare topping: In a small bowl, mix melted butter and brown sugar. Spoon about 1 teaspoon into the bottom of each muffin cup.

  3. Add fruit: Place a pineapple ring (cut to fit, if needed) into each cup and add a cherry in the center.

  4. Make cookie dough: In a large bowl, cream together butter, granulated sugar, and brown sugar until light and fluffy. Add egg and vanilla; mix well.

  5. Combine dry ingredients: In another bowl, whisk flour, baking powder, baking soda, and salt. Gradually add to wet mixture until fully incorporated.

  6. Assemble: Drop a spoonful of cookie dough on top of the pineapple and gently press to flatten.

  7. Bake for 14–16 minutes, or until edges are golden and cookies are set.

  8. Cool and flip: Let cookies cool in the tin for 5 minutes. Carefully flip each one onto a wire rack or tray while still warm to release the topping.

Notes

  • Use paper towels to dry pineapple slices before placing them in the pan to prevent sogginess.
  • You can use crushed pineapple instead of rings for a different presentation.
  • Store leftovers in an airtight container for up to 3 days.
  • Prep Time: PT20M
  • Cook Time: PT16M
  • Category: Dessert
  • Method: Baking
  • Cuisine: American