Pineapple Upside-Down Sugar Cookies
If you love the charm of a pineapple upside-down cake but want something easier to grab and go, these cookies are the sweetest little twist. Each one has a buttery brown sugar bottom, a juicy pineapple ring, a bright cherry center, and a soft sugar cookie baked right on top. They’re fun, nostalgic, and just messy enough to feel indulgent—perfect for summer gatherings or a bright treat any time of year.
Ingredients
Cookie Dough
- 1 cup unsalted butter, room temperature
- 1½ cups granulated sugar
- 2 large eggs
- 2 tsp vanilla extract
- ½ cup sour cream
- 3 cups all-purpose flour
- 1 tsp baking powder
- 1 tsp cornstarch
- ½ tsp salt
Topping
- 13 canned pineapple slices
- 13 maraschino cherries
- ½ cup unsalted butter, melted
- 1 cup packed light brown sugar
Instructions
Prep the Pan & Oven
Preheat your oven to 350°F. Grab a USA Pan mini round cake pan (or similar style) and set it aside—no lining or greasing needed.
Make the Cookie Dough
In a large mixing bowl, cream the softened butter and sugar together until light and fluffy.
Add the eggs, vanilla, and sour cream, mixing until everything is incorporated.
Stir in the flour, baking powder, cornstarch, and salt just until the dough comes together. Don’t overmix. Set aside.
Prep the Brown Sugar Layer
In a small bowl, combine the melted butter and brown sugar until evenly blended.
Spoon about 1 tablespoon of this mixture into the bottom of each well in the pan, spreading to coat the base.
Assemble the Cookies
Place one pineapple slice over the brown sugar layer, then add a cherry in the center of each ring.
Scoop about 3 tablespoons of cookie dough over the pineapple (a large cookie scoop works great).
Use a small offset spatula to gently flatten the dough so it covers the fruit.
Bake
Bake for about 25 minutes, or until the edges are golden and you can see the brown sugar bubbling up the sides.
Cool & Flip
Let the cookies rest in the pan for 10 minutes. Then carefully invert them onto a sheet of wax paper—don’t skip the wax paper, because the glaze will run a bit.
If any pineapple sticks to the pan, just place it back on the cookie while it’s still warm.
Serve & Store
Allow to cool completely before serving. Store in an airtight container. These taste best within 2–3 days.
