1-First Step: Get the pan and oven ready Start by preheating your oven to 350 degrees. Then prepare a mini round cake pan so it is ready for the cookie layers. This part matters because the brown sugar and butter mixture will start working fast once it is mixed, and you want to move quickly while everything is still easy to spread. If your pan has cavities that are a little stubborn, give them a light coating if needed so the finished cookies release more easily. This recipe depends on the pretty pineapple topping turning out cleanly, so a little prep here saves a lot of fuss later.

2-Second Step: Mix the cookie dough In a large mixing bowl, beat together the room temperature butter and 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. If you are mixing by hand, it will take a little more elbow grease, but it will still work just fine. Next, add the eggs, vanilla extract, and sour cream. Mix until everything is combined. The dough will look smooth and creamy, and that is exactly what you want before adding the dry ingredients. If you are using Greek yogurt instead of sour cream, this is the spot where it goes in.

3-Third Step: Finish the dough Add the flour, baking powder, cornstarch, and salt to the bowl. Mix until a dough forms. At first, it may look crumbly, but keep going until it comes together. Avoid overmixing once the flour is in, since too much mixing can make the cookies tougher than you want. The dough should be soft and workable. If it feels sticky, let it rest for a few minutes before shaping. This can make assembly easier, especially if your kitchen is warm or if the butter softened a little too much.

4-Fourth Step: Build the pineapple topping In another bowl, stir the melted butter and packed light brown sugar until combined. This mixture is the sticky, sweet layer that gives the cookies their upside down cake flavor. Spoon about 1 tablespoon of the brown sugar mixture into the bottom of each cavity in the mini round cake pan and spread it out. Place one pineapple slice on top of the brown sugar mixture in each cavity, then add a maraschino cherry in the center of each slice. This is the part that makes the cookies so fun to serve because every piece looks like its own tiny dessert.

5-Fifth Step: Add the cookie dough and bake Scoop about 3 tablespoons of cookie dough onto each pineapple slice. Flatten the dough gently with an offset spatula so it covers the fruit and fills the cavity. You do not need to press it perfectly smooth, but you do want an even layer so the cookies bake consistently. Bake for about 25 minutes, or until the edges are golden brown and the brown sugar bubbles up the sides. Keep an eye on them during the last few minutes. The tops should look set, and the kitchen will smell like warm butter, caramel, and pineapple.

6-Final Step: Cool and turn out the cookies Let the cookies cool in the pan for 10 minutes after baking. This short rest helps the topping settle a bit so the cookies are easier to release. Then turn them out onto wax paper and let them cool completely before eating. Patience pays off here, even though it is tempting to grab one right away. Once fully cooled, the cookies hold together better and the pineapple topping stays prettier. Store them in an airtight container so they stay fresh.