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Pineapple Upside-Down Cookie Bars with Cherry Glaze

Pineapple Upside-Down Cookie Bars - featured image
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These Pineapple Upside-Down Cookie Bars transform the classic cake into chewy, golden bars topped with caramelized pineapple and a tangy cherry glaze. Perfect for parties, potlucks, or a fun family dessert, they’re easy to make and always a crowd-pleaser.

Ingredients

Scale
  • 1/4 cup unsalted butter, melted (for pineapple layer)
  • 1/2 cup packed light brown sugar (for pineapple layer)
  • 1 can (20 oz) pineapple slices in juice, drained (reserve juice for glaze)
  • 10–12 maraschino cherries (whole, for topping pineapple)
  • 1/2 cup unsalted butter, softened (for cookie base)
  • 3/4 cup granulated sugar
  • 1/4 cup packed light brown sugar (for cookie base)
  • 2 large eggs, room temperature
  • 2 tsp vanilla extract
  • 1 3/4 cups all-purpose flour (or gluten-free blend)
  • 1/2 tsp baking powder
  • 1/4 tsp baking soda
  • 1/4 tsp salt
  • 1/2 cup reserved pineapple juice (for glaze)
  • 1/3 cup maraschino cherries, chopped (for glaze)
  • 1 cup powdered sugar (for glaze)
  • 1/2 tsp almond extract (optional, for glaze)

Instructions

  1. Line a 9×13 inch baking pan with parchment paper, leaving an overhang for easy lifting. Lightly grease the sides.
  2. Pour melted butter over the parchment, then sprinkle brown sugar evenly on top. Arrange pineapple slices in a single layer, trimming if needed. Place a maraschino cherry in the center of each pineapple ring.
  3. In a large bowl, beat softened butter, granulated sugar, and brown sugar until creamy (about 2 minutes). Add eggs and vanilla extract, mixing until smooth.
  4. In a separate bowl, whisk together flour, baking powder, baking soda, and salt. Gradually add dry ingredients to wet, mixing until just combined.
  5. Gently dollop cookie dough over the pineapple layer, then spread evenly with a spatula. Bake at 350°F for 25-30 minutes, until edges are golden and a toothpick inserted in the center comes out mostly clean.
  6. Let the pan cool for 10-15 minutes on a wire rack. Carefully lift bars out using parchment overhang. Place a cutting board on top, then invert so pineapple layer faces up. Peel off parchment gently.
  7. In a small bowl, combine reserved pineapple juice, chopped cherries, powdered sugar, and almond extract (if using). Whisk until smooth and glossy. Adjust consistency with more powdered sugar or juice as needed.
  8. Drizzle cherry glaze all over the cooled bars. Optionally, add a few chopped cherries on top. Slice into squares (about 20 bars).

Notes

For gluten-free, use a 1:1 blend. For dairy-free, use plant-based butter. Drain pineapple well to avoid soggy bars. Chill bars before cutting for neat squares. Glaze consistency can be adjusted with more powdered sugar or juice. Bars freeze well before glazing.

Nutrition

Keywords: pineapple upside-down bars, cookie bars, cherry glaze, easy dessert, potluck, party treat, pineapple dessert, retro dessert, chewy bars, fruit bars

Find it online: https://bitefuljoy.com/pineapple-upside-down-cookie-bars-recipe-easy-cherry-glaze-dessert/