Looking for a treat that’s both nostalgic and refreshingly new? Pineapple Upside Down Sugar Cookies capture the sweet, caramelized goodness of classic pineapple upside down cake, but in a cute, handheld cookie. Imagine biting into a tender, buttery sugar cookie topped with a juicy pineapple ring — every bite is a burst of sunny flavor that’s equal parts fun and satisfying. Did you know upside down cakes became trendy in the 1920s, thanks in part to the rise of canned pineapple? Fast forward to today, and these cookies borrow that retro charm while cutting down on the mess and prep time.

Ingredients

• 1 cup Unsalted Butter, softened
• 1 cup Granulated Sugar
• 1 large Egg
• 1 teaspoon Vanilla Extract
• 2 cups All-Purpose Flour
• 1 teaspoon Baking Soda
• 1/2 teaspoon Salt
• 10-12 rings Canned Pineapple, well-drained and patted dry
• to taste Additional Sugar for Sprinkling

Instructions

1. Preheat your oven to 350°F (180°C). Line baking trays with parchment paper for easy cleanup.
2. Using a large mixing bowl, cream together the softened butter and sugar until light and fluffy, about 2-3 minutes with an electric mixer.
3. Beat in the egg and vanilla extract until well combined and smooth.
4. In a separate bowl, whisk together flour, baking soda, and salt. Gradually add the dry ingredients to the wet ingredients, mixing just until a soft dough forms.
5. Scoop about 2 tablespoons of dough per cookie onto the prepared baking trays, spacing them 2 inches apart.
6. Gently press a dried pineapple ring onto each mound of cookie dough, flattening slightly. Trim or halve the rings if necessary.
7. Sprinkle a bit of granulated sugar over the pineapple tops for a touch of sparkle and caramelization.
8. Bake for 11-13 minutes, or until the cookies are lightly golden around the edges and set in the center.
9. Allow cookies to cool on the baking tray for a few minutes before transferring to a wire rack to cool completely. Enjoy!