1-First Step: Prep the pan and oven Preheat your oven to 350 degrees F. Prepare your pan before anything else so the brown sugar topping does not sit around and get sticky in the wrong places. A muffin tin or similar cavity-style pan works well for this style of cookie because it helps hold the pineapple and caramel layer in place. This is the part where a little prep saves you from a sugary mess later.

2-Second Step: Make the cookie dough In a large bowl, cream together the 1 cup room temperature butter and 1.5 cups granulated sugar until the mixture looks light and fluffy. Add the 2 eggs, 2 teaspoons vanilla extract, and 0.5 cup sour cream, then mix until everything is blended. The batter should look smooth and creamy, which is exactly what you want for soft Pineapple Upside Down Sugar Cookies.

3-Third Step: Add the dry ingredients Stir in the 3 cups flour, 1 teaspoon baking powder, 1 teaspoon cornstarch, and 0.5 teaspoon salt. Mix just until a dough forms. Do not beat it to death here. Overmixing can make cookies tough, and nobody wants a cookie with commitment issues.

4-Fourth Step: Mix the caramel topping In a separate bowl, stir together the 0.5 cup melted butter and 1 cup packed light brown sugar. This topping should look thick and glossy. Spoon about 1 tablespoon of the mixture into each pan cavity and spread it across the bottom. That layer is what creates the bubbling, sticky magic once the cookies bake.

5-Fifth Step: Add the pineapple and cherry Place 1 canned pineapple slice into each cavity, then top each slice with 1 maraschino cherry. The pineapple should sit right on the brown sugar layer. If you are using canned pineapple, drain it well so the topping does not turn watery. That little detail keeps the cookies from getting soggy.

6-Sixth Step: Add the dough Scoop about 3 tablespoons of dough onto each pineapple slice and flatten it gently. The recipe may yield more than 13 cookies even with this amount, so if you have a little extra dough, bake it in a second round or make a few plain sugar cookies on the side. The dough should cover the topping enough to bake into a neat cookie base without spilling too much.

7-Seventh Step: Bake until golden Bake for about 25 minutes, or until the edges are golden and the brown sugar bubbles around the sides. The top should look set, but not overly browned. If your oven runs hot, start checking a few minutes early because nobody wants a cookie with a scorched bottom and an attitude.

8-Eighth Step: Turn out and cool Let the cookies cool in the pan for 10 minutes. Then turn them out onto wax paper so the brown sugar runoff has somewhere to go. If a pineapple slice sticks, gently reposition it back on top of the cookie. Let the cookies cool completely before serving so the caramel layer can settle. That is how you get the best texture and the prettiest finish.