Step 3: Make the Sugar Cookie Dough
In a large mixing bowl, cream the softened butter and granulated sugar together until light and fluffy. This step helps create a soft cookie texture.
Add the egg and vanilla extract, mixing until fully combined.
In a separate bowl, whisk together the flour, baking powder, and salt. Gradually add the dry ingredients to the wet mixture, mixing just until a soft dough forms. Avoid overmixing to keep the cookies tender.
Step 4: Assemble the Cookies
Scoop about 1½ tablespoons of cookie dough and gently flatten it slightly with your hands. Place the dough over the pineapple topping in each muffin cup. Lightly press to cover the fruit without pushing it down too firmly.
Step 5: Bake to Golden Perfection
Bake the cookies for 13–16 minutes, or until the cookie edges are lightly golden and set. The centers should look soft but not wet.
Step 6: Flip and Reveal
Remove the pan from the oven and let the cookies cool for 5 minutes. Run a knife gently around the edges, then carefully invert the pan onto a baking sheet or cooling rack.
Lift the pan slowly to reveal the glossy pineapple tops. Let the cookies cool completely before serving.
Helpful Tips for Success
- Drain the pineapple well to prevent soggy cookies
- Invert while warm so the caramel releases cleanly
- Use room-temperature butter for smoother cookie dough
- Don’t overbake—soft cookies pair best with the caramel topping
Storage and Serving
Store Classic Pineapple Upside-Down Sugar Cookies in an airtight container in the refrigerator for up to 3 days. Bring to room temperature before serving for the best flavor and texture.
These cookies are delicious on their own or served with a scoop of vanilla ice cream for an extra-special dessert.
Final Thoughts
Classic Pineapple Upside-Down Sugar Cookies are a delightful blend of nostalgia and creativity. With their golden caramel topping, juicy pineapple, and soft sugar cookie base, they offer a fun new way to enjoy a beloved classic. Whether you’re baking for family, friends, or a special occasion, these cookies are guaranteed to impress—both in flavor and presentation.
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