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Pineapple Upside-Down Sugar Cookies

Delicious and easy-to-make cookies with a sunny caramelized pineapple topping and buttery edges, perfect for those who want a simpler dessert.
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Prep Time 15 minutes
Cook Time 15 minutes
Total Time 30 minutes
Servings: 12 cookies
Course: Dessert, Snack
Cuisine: American
Calories: 150
Ingredients Method Notes

Ingredients
  

Topping
  • 4 tablespoons Butter Melted for topping
  • 1/2 cup Brown sugar
  • 1 pinch Salt Add to the topping mixture
  • 12 halves Maraschino cherries For the center of the cookies
  • 12 slices Pineapple Well drained; for topping
Cookie Dough
  • 1/2 cup Butter Room temperature for the dough
  • 1/2 cup Granulated sugar
  • 1 Egg
  • 1 teaspoon Vanilla extract
  • 1 1/2 cups All-purpose flour
  • 1 teaspoon Baking powder
  • 1 pinch Salt For the dough
  • 1 tablespoon Cornstarch Optional for extra softness

Method
 

Prepare the Topping
  1. Melt butter in a small bowl, then stir in brown sugar and a pinch of salt until it resembles wet sand.
  2. Spoon a small amount into each muffin cup.
  3. Press a cherry half in the center of each and tuck a small wedge of pineapple on top.
Make the Cookie Dough
  1. Cream room temperature butter with granulated sugar until light and fluffy.
  2. Add the egg and vanilla extract, mixing well.
  3. In a separate bowl, whisk together flour, baking powder, and salt.
  4. Mix the dry ingredients into the wet until just combined, avoiding overmixing.
  5. If dough is too sticky, chill for 10-15 minutes.
  6. Optionally, mix in cornstarch for added tenderness.
Assemble and Bake
  1. Scoop dough balls and gently press them over the pineapple layer in each muffin cup.
  2. Bake until edges are golden and centers are set.
  3. Let cool for a couple of minutes, then carefully run a knife around each cookie.
  4. Flip the pan onto parchment while warm to let the topping slide over the cookies.

Notes

Store cookies in an airtight container at room temperature for up to two days. For longer storage, freeze in a single layer, then bag. Optional variations include using almond extract or coconut in the topping.