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Pineapple Upside Down Cake Cookies

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Warm, buttery cookies topped with juicy pineapple and a cherry in the center, these pineapple upside down cake cookies combine the nostalgic flavors of classic cake with the fun, snackable joy of cookies. Perfect for parties, bake sales, or whenever you need a little sunshine on your plate.

Ingredients

Scale
  • 1 cup (226g) unsalted butter, softened
  • 1 cup (200g) packed brown sugar
  • 1/2 cup (100g) granulated sugar
  • 2 large eggs, room temperature
  • 2 teaspoons pure vanilla extract
  • 2 3/4 cups (345g) all-purpose flour
  • 1/2 teaspoon salt
  • 1 teaspoon baking powder
  • 1/2 teaspoon baking soda
  • 1 can (20 oz/565g) pineapple slices, drained well and patted dry
  • Maraschino cherries, halved (about 12–16, depending on cookie size)
  • 1/4 cup (50g) packed brown sugar (for sprinkling under fruit)
  • 1 cup (120g) powdered sugar (optional glaze)
  • 1–2 tablespoons reserved pineapple juice or milk (optional glaze)

Instructions

  1. Preheat oven to 350°F (175°C). Line two baking sheets with parchment paper or silicone baking mats.
  2. Drain pineapple slices very well and pat dry with paper towels. Cut pineapple rings into quarters or halves, depending on cookie size. Halve the cherries.
  3. In a large mixing bowl, cream together softened butter, brown sugar, and granulated sugar until light and fluffy (about 2-3 minutes with a mixer).
  4. Add eggs, one at a time, mixing well after each. Stir in vanilla extract.
  5. In a separate bowl, whisk together flour, salt, baking powder, and baking soda.
  6. Gradually add the dry mixture to the wet ingredients, mixing just until combined. Do not overmix.
  7. Using a cookie scoop or two spoons, portion about 2 tablespoons of dough per cookie onto lined baking sheets, spacing at least 2 inches apart.
  8. Gently flatten each ball with your palm or the bottom of a glass.
  9. Sprinkle a pinch of brown sugar (from the 1/4 cup reserved for topping) on top of each cookie.
  10. Press a piece of pineapple and a cherry half into the center of each cookie.
  11. Bake for 12–15 minutes, until edges are golden and centers look just set. Rotate pans halfway through for even browning.
  12. Let cookies cool on the tray for 5 minutes, then transfer to a wire rack to cool completely.
  13. For optional glaze: Mix powdered sugar with 1–2 tablespoons reserved pineapple juice or milk until smooth. Drizzle over cooled cookies and let set for 10 minutes before serving.

Notes

Dry pineapple slices thoroughly to prevent soggy cookies. For thicker, chewier cookies, chill the dough for 30 minutes before baking. Rotate pans halfway through baking for even browning. Cookies can be made gluten-free or vegan with simple substitutions. Store in an airtight container at room temperature for up to 3 days, or freeze for up to 2 months.

Nutrition

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