
Pineapple Upside-Down Sugar Cookies
- Prep the pans
Preheat oven to 350°F (175°C).
Spray a 12-cup muffin tin with nonstick spray (or grease well).
- Make the caramel topping
In a small bowl, mix melted butter and brown sugar.
Place about 1 tablespoon of the mixture into each muffin cup.
Add a pineapple ring on top, trimming to fit if needed.
Place a maraschino cherry in the center hole of each ring.
- Make the cookie dough
In a large mixing bowl, beat the butter and sugar together until light and fluffy (about 2 minutes).
Beat in the egg and vanilla until smooth.
In a separate bowl, whisk together the flour, baking soda, baking powder, and salt.
Gradually mix dry ingredients into the wet until just combined.
- Assemble
Scoop about 2 tablespoons of cookie dough and flatten slightly into a disk.
Place over each pineapple-cherry setup in the muffin cups, spreading gently to cover.
- Bake
Bake for 18–22 minutes, or until the cookies are golden and set.
Let cool for 5 minutes only (important – they’ll stick if too cool).
- Invert & serve





