Description

These Pineapple Upside-Down Sugar Cookies are a fun twist on the classic cake! Made with soft sugar cookie dough, caramelized pineapple slices, and cherries, they deliver all the nostalgic flavors in a bite-sized treat. Perfect for parties, potlucks, or when you just want a tropical dessert in cookie form.

Ingredients

1/2 cup unsalted butter, softened
1 cup granulated sugar
1 large egg
1 tsp vanilla extract
1 1/2 cups all-purpose flour
1/2 tsp baking soda
1/4 tsp salt
1/2 cup packed light brown sugar
6 canned pineapple rings, cut into small pieces
6 maraschino cherries, halved

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Instructions

Preheat your oven to 350°F (175°C). Lightly grease or line a muffin tin with nonstick spray.
In a small bowl, mix the brown sugar with 2 tablespoons of melted butter. Spoon about a teaspoon of this mixture into each muffin cup.
Place a few small pieces of pineapple and half a maraschino cherry in the center of each cup on top of the brown sugar mix.
In a large bowl, cream together the softened butter and granulated sugar until light and fluffy.
Beat in the egg and vanilla extract.
In a separate bowl, whisk together the flour, baking soda, and salt. Gradually add the dry ingredients to the wet mixture, mixing just until combined.
Scoop about 2 tablespoons of dough and flatten it slightly. Place it over the pineapple in each muffin cup, pressing lightly.
Bake for 15–18 minutes, or until the edges are golden brown.
Let the cookies cool in the pan for about 5 minutes, then carefully flip them out onto a wire rack to cool completely.

Notes

Be sure to grease your muffin tin well so the cookies release easily.
You can use fresh pineapple, but canned works best for consistency.
These are best served the same day but can be stored in an airtight container for up to 2 days.

Nutrition

Serving Size: 1 cookie
Calories: 190
Sugar: 18g
Sodium: 85mg
Fat: 8g
Saturated Fat: 5g
Unsaturated Fat: 2g
Trans Fat: 0g
Carbohydrates: 28g
Fiber: 0.5g
Protein: 2g
Cholesterol: 25mg