1-First Step: Get your oven and pans ready Preheat your oven to 350 degrees Fahrenheit. This gives the oven time to reach the right temperature while you make the dough. Next, grab mini round cake pans and set them aside. These pans are the key to the cookie’s neat little upside-down shape, so do not skip them unless you enjoy dessert chaos, which I do not recommend. Because this recipe bakes quickly, it helps to have everything within arm’s reach. Open the pineapple slices, drain the cherries if needed, and measure all ingredients before mixing. That little bit of prep makes the whole process smoother and keeps you from scrambling for flour with sticky hands later.

2-Second Step: Cream the butter and sugar In a large mixing bowl, mix 1 cup room temperature butter and 1 1/2 cups granulated sugar until the mixture looks light and fluffy. This step adds air to the dough, which helps the cookies bake up soft instead of heavy. Use a hand mixer or stand mixer if you have one, or stir with a sturdy spoon if you want a mini arm workout. Once the butter and sugar look creamy, add 2 eggs, 2 teaspoons vanilla extract, and 1/2 cup sour cream. Mix until everything is combined. The batter should look smooth and rich, with no streaks of sour cream hanging around like it forgot to join the party.

3-Third Step: Add the dry ingredients In the same bowl, add 3 cups flour, 1 teaspoon baking powder, 1 teaspoon cornstarch, and 1/2 teaspoon salt. Mix until the cookie dough just comes together. Stop as soon as you no longer see dry flour. Overmixing can make the cookies tough, and nobody wants a grumpy cookie. If the dough seems a little thick, that is perfectly fine. It should be scoopable and soft enough to press into the pans without running everywhere. Since the recipe is meant for mini cake pans, the dough does not need to be rolled or cut, which saves time and keeps cleanup easier.

4-Fourth Step: Make the brown sugar topping In a separate bowl, stir together 1/2 cup melted butter and 1 cup packed light brown sugar until combined. This mixture is the sweet, sticky layer that turns into that gorgeous caramel-like topping while baking. It is the kind of topping that makes people peek into the oven every few minutes like they are waiting for treasure. Add about 1 tablespoon of the brown sugar mixture into the bottom of each mini round cake pan cavity and spread it around. This does not need to be exact to the last drop, but try to give each pan a nice even layer. That way, every cookie gets the same sticky finish.

5-Fifth Step: Add pineapple and cherries Place one pineapple slice on top of the brown sugar in each pan cavity. Then add one maraschino cherry in the center of the pineapple. This gives you the classic pineapple upside down look and makes each cookie feel like its own tiny dessert centerpiece. If your pineapple slices are large, you can position them carefully so they fit the pan well. Since the recipe uses canned pineapple, the slices are convenient and consistent, which is great when you want a dessert that behaves itself.

6-Sixth Step: Top with cookie dough Scoop about 3 tablespoons of cookie dough and place it on top of each pineapple slice. Use an offset spatula to flatten it out gently so it covers the fruit and reaches the edges of the pan. The dough should sit right on top like a cozy little blanket. The recipe may make more than 13 cookies, even with 3 tablespoons of batter in each one. If you have extra dough, you can bake another round or make a bonus cookie or two. Honestly, extra cookie dough is never a problem in my kitchen.

7-Seventh Step: Bake until golden Bake for about 25 minutes, or until the edges are golden brown and the brown sugar is bubbling up the sides. The smell alone will probably bring people into the kitchen asking if it is ready yet. That bubbling topping is the sign you want, so keep an eye on the color near the end of the bake time. Every oven behaves a little differently, so start checking near the end of baking. If the tops are set and the edges have that warm golden color, you are in good shape. Total time for the recipe is about 45 minutes, with 20 minutes of prep and 25 minutes of baking.

8-Eighth Step: Cool and turn out Let the cookies cool for 10 minutes in the pans. This short rest helps the topping settle and makes it easier to flip them out without breaking the fruit layer. After that, turn them out onto a wax paper-covered surface. If a pineapple slice sticks to the pan, just reposition it on top of the cookie. No one is grading your flip technique, so do not panic if one cookie needs a little cosmetic help. Let the cookies cool completely before eating so the topping can set properly and the texture stays nice.

9-Final Step: Serve and store Once cooled, serve the cookies as-is or with a small spoonful of whipped cream if you want to get fancy. They are sweet, soft, and sticky in the best possible way. Since these cookies are best eaten within 2 to 3 days, they make a great short-term treat for family snacking or a small gathering. Store leftovers in an airtight container at room temperature. If you need a full recipe summary, here is a quick look: