Pineapple Upside Sugar Cookies – Page 2

1. Prep the Oven & Pan:
Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper.

2. Create the Caramelized Topping:

If using fresh pineapple, pat the rings dry with a paper towel to remove excess moisture.
Brush one side of each pineapple ring with the melted butter.
In a small bowl, mix the brown sugar and cinnamon (if using). Sprinkle this mixture evenly over the buttered side of the pineapple rings.
Place the rings, sugar-side down, on the prepared baking sheet.

3. Make the Cookie Dough:

In a large bowl, using an electric mixer or a wooden spoon, cream together the softened butter and granulated sugar until light and fluffy.
Beat in the egg and vanilla extract until the mixture is smooth and well-combined.
In a separate bowl, whisk together the flour, baking powder, and salt.
Gradually add the dry ingredients to the wet ingredients, mixing on low speed until just combined. Be careful not to overmix.

4. Assemble the Cookies:

Scoop about 1-2 tablespoons of dough and flatten it slightly into a disc in your hand.
Gently place each dough disc on top of a pineapple ring, pressing lightly to cover the ring completely.

5. Bake to Perfection:

Bake for 12-15 minutes, or until the cookie edges are lightly golden.
Allow the cookies to cool on the baking sheet for 5 minutes. This is crucial for them to set.

6. The Grand Reveal:

After the 5-minute rest, carefully flip each cookie over so the caramelized pineapple is on top. Use a spatula for support.
Let them cool completely on a wire rack.

Fresh vs. Canned: Fresh pineapple offers a brighter, tarter flavor and caramelizes beautifully. Canned rings are a fantastic shortcut—just be sure to drain them thoroughly.
Add Some Texture: For a delightful crunch, sprinkle chopped macadamia nuts or pecans over the pineapple topping before adding the cookie dough.
Drizzle for Glamour: A simple glaze made from powdered sugar and a little milk or pineapple juice drizzled over the cooled cookies adds a beautiful finish.
Storage: Store these cookies in an airtight container at room temperature for up to 2 days. For longer storage, refrigerate for up to 5 days. Let them come to room temperature before serving for the best texture and flavor.