1-Step 1: Get the pan and oven readyPreheat your oven to 350 degrees Fahrenheit. Then prepare a mini round cake pan so each cavity is ready for the brown sugar, pineapple, and cookie dough. This step matters because the topping needs a snug place to bake and release cleanly later. If your pan tends to stick, a light coating of nonstick spray can help.

2-Step 2: Mix the cookie doughIn a large mixing bowl, mix 1 cup room temperature butter with 1 1/2 cups granulated sugar until the mixture looks light and fluffy. Add 2 eggs, 2 teaspoons vanilla extract, and 1/2 cup sour cream, then mix until everything is fully combined. This is the part where the dough starts to feel smooth and rich, which is exactly what you want for Pineapple Upside Down Sugar Cookies.Next, add 3 cups flour, 1 teaspoon baking powder, 1 teaspoon cornstarch, and 1/2 teaspoon salt. Mix just until the dough forms. Try not to overmix here, because that can make the cookies tougher than you want. The dough should be soft but easy to scoop.

3-Step 3: Make the caramel-like toppingIn another bowl, stir together 1/2 cup melted butter and 1 cup packed light brown sugar until combined. This is the sweet base that gives the cookies their upside down cake style flavor. If the mixture seems a little loose, that is okay. It will bake into a bubbly, golden layer in the oven.Add about 1 tablespoon of the brown sugar mixture to the bottom of each pan cavity and spread it out. This does not need to be perfect, but do try to cover the bottom evenly so every cookie gets that sticky finish.

4-Step 4: Add the pineapple and cherryPlace 1 canned pineapple slice on top of the brown sugar mixture in each cavity. Then place 1 maraschino cherry right in the center of each pineapple slice. That classic red center makes these cookies extra fun and cheerful. If you are making them for kids, this part is often their favorite.

5-Step 5: Add the doughScoop about 3 tablespoons of cookie dough on top of each pineapple slice. Flatten gently with an offset spatula so the dough covers the fruit without pressing it too hard. You want enough dough to bake into a soft cookie top, but not so much that the fruit gets buried completely.If your mini cake pan cavities are a bit larger or smaller, adjust the dough slightly. The recipe may yield a little more than 13 cookies, so do not worry if you have extra dough. That is a good excuse for a bonus cookie or two.

6-Step 6: Bake until goldenBake for about 25 minutes, or until the edges turn golden brown and the brown sugar begins to bubble around the fruit. The kitchen will smell amazing, by the way. That warm pineapple and butter smell is pretty hard to ignore.If you like checking doneness carefully, look for lightly set centers and browned edges. The cookies should be baked through, but still soft enough to feel tender when cooled.

7-Step 7: Cool and turn outLet the cookies cool for 10 minutes in the pan. Then turn them out onto wax paper. This part is important because turning them out too soon can make the topping slide. If pineapple sticks to the pan, simply reposition it on the cookie. A small nudge usually fixes it.Cool completely before eating so the topping sets a little. Once cooled, store them in an airtight container. These Pineapple Upside Down Sugar Cookies are at their best when the topping stays neat and the cookie stays soft.