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Pineapple upside down sugar cookies topped with cherries and pineapple slices

Pineapple Upside Down Sugar Cookies

These delightful sugar cookies topped with well-drained pineapple rings combine buttery sweetness with a tropical twist, perfect for summer gatherings.
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Prep Time 20 minutes
Cook Time 12 minutes
Total Time 32 minutes
Servings: 24 cookies
Course: Dessert, Snack
Cuisine: American
Calories: 160
Ingredients Method Notes

Ingredients
  

Cookie Base
  • 1 cup unsalted butter (softened) Softened, not melted. Room temperature butter gives the best texture for sugar cookies.
  • 1 cup granulated sugar
  • 1 large egg
  • 1 teaspoon vanilla extract (optional)
  • 2 cups all-purpose flour (or gluten-free blend) Use a 1:1 gluten-free blend if needed; make sure it’s an all-purpose variety that’s designed for baking.
  • 1 teaspoon baking soda
  • ½ teaspoon salt
Topping
  • 1 can canned pineapple rings (well-drained) Well-drained canned rings are convenient, but fresh or roasted pineapple options are available.
  • 2 tablespoons additional sugar for sprinkling This helps create a quick glaze/caramel effect on the pineapple during baking.

Method
 

Preparation
  1. Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper or a silicone mat. Ensure your pineapple rings are well-drained.
  2. In a large bowl or stand mixer, cream the softened butter with granulated sugar until light and fluffy, about 2–3 minutes.
  3. Beat in the egg and optional vanilla extract until fully incorporated. Scrape the bowl down once to mix evenly.
  4. In a separate bowl, whisk flour, baking soda, and salt. Gradually add the dry mixture to the butter mixture and mix until just combined.
  5. Use a cookie scoop to portion dough into walnut-sized balls and place them on the prepared baking sheet about 2 inches apart.
  6. Flatten each ball gently to about 1/2-inch thick and press a pineapple coin gently into the center of each cookie.
  7. Sprinkle each pineapple-topped cookie lightly with the additional sugar.
Baking
  1. Bake for 10–12 minutes until the edges are turning golden and the pineapple is bubbling.
  2. Invert the tray onto a cooling rack so the cookies land pineapple-side up, creating a glazed surface.
  3. Let cookies cool fully for 10–15 minutes.
Serving
  1. Transfer cooled cookies to a platter and serve warm, at room temperature, or slightly chilled.

Notes

For a deeper caramelization of the pineapple, gently torch the tops or broil for 30–60 seconds, watching closely. You can make ahead by freezing the dough or baked cookies.