Pineapple Upside-Down Sugar Cookies

Chill the Dough: This helps cookies keep their shape.
Smaller Pineapple: Cut rings into smaller pieces if needed.
Avoid Overbaking: Remove when edges are lightly golden to keep them soft.

Cream together softened butter and granulated sugar until light and fluffy (2-3 minutes).
Beat in the egg and vanilla extract until well combined.
Whisk together flour, baking soda, and salt. Gradually add to wet ingredients, mixing until just combined. Cover and chill for at least 30 minutes.

In a skillet over medium heat, melt 1 tablespoon butter. Add brown sugar and stir until melted and combined (1-2 minutes).
Add pineapple rings and cook for about 2 minutes per side, until lightly caramelized. Remove from heat and cool slightly.

Preheat oven to 350°F (175°C). Line a baking sheet with parchment paper.
Scoop 1 1/2 tablespoons of chilled dough, roll into a ball, and flatten slightly on the baking sheet.
Top each cookie with a caramelized pineapple piece and a maraschino cherry half.

Bake for 12-15 minutes, or until edges are lightly golden.
Cool on the baking sheet for 5 minutes, then transfer to a wire rack to cool completely.

Store in an airtight container at room temperature for up to 3 days, or refrigerate for up to 5 days.

Yes! Cut into small, even pieces and caramelize as directed.

Yes! Make and refrigerate up to 24 hours before baking. Let it sit at room temperature for a few minutes if too firm.

Yes, for up to 2 months. Thaw at room temperature before serving.

These Pineapple Upside-Down Sugar Cookies are a delightful tropical treat! Enjoy!