- Preheat the Oven – 350°F (175°C).
- Prepare the Topping – In each cup of a greased muffin tin, spoon about 1 tsp melted butter and 1 tsp brown sugar. Place a pineapple piece (and a cherry, if using) on top.
- Make the Cookie Dough – Cream butter and sugar until fluffy. Add egg and vanilla; mix well. In another bowl, whisk flour, baking powder, and salt, then gradually add to the wet ingredients.
- Assemble – Roll cookie dough into balls (about 1½ inches) and gently press on top of the pineapple layer in the muffin cups. Flatten slightly.
- Bake – 12–15 minutes, until edges are lightly golden.
- Flip and Reveal – Cool for 5 minutes, then carefully invert the muffin tin onto a baking sheet so the pineapple side is facing up.
The First Bite Experience
Your teeth sink into the chewy cookie, followed by a burst of warm pineapple juice and a deep caramel sweetness from the brown sugar glaze. It’s soft, sticky, sweet, and tangy all at once — pure dessert bliss in two bites.
Tips for the Perfect Pineapple Upside Sugar Cookies
- Use canned pineapple in juice, not syrup, to keep the sweetness balanced.
- Pat pineapple dry before adding to prevent excess moisture in the cookies.
- For a fancier look, cut pineapple into perfect circles and place a cherry right in the center.
Why You’ll Make These Again
They’re beautiful enough for parties, simple enough for weeknight baking, and unique enough to get people talking. Plus, they taste like summer — even in the middle of winter.
Once you make Pineapple Upside Sugar Cookies, they’ll become one of your signature desserts.