1-Step 1: Preheat and prep the pan Start by heating your oven to 350 degrees F. Prepare your pan so you are ready to build each cookie without scrambling around later. A muffin pan works best because it gives the topping a neat shape and helps the cookies bake in tidy portions. Since the brown sugar mixture gets sticky fast, it helps to have all your ingredients measured before you start. That way, when the dough is ready, you can move through the pan assembly without rushing like you are late for a school bake sale.

2-Step 2: Cream the butter and sugar In a large mixing bowl, beat 1 cup butter and 1 1/2 cups granulated sugar until the mixture looks light and fluffy. This step matters because it helps create a softer cookie with a nice, even crumb. If your butter is truly room temperature, this part goes much more smoothly. Take your time here. A good cream leads to a better texture, and these pineapple upside down sugar cookies are at their best when the base is soft and tender.

3-Step 3: Add the wet ingredients Mix in 2 eggs, 2 tsp vanilla extract, and 1/2 cup sour cream until everything is fully combined. The sour cream adds moisture and a gentle tang that balances all the sweetness. If you like baking with a little extra richness, this part is where the dough starts to feel special. If you need to use Greek yogurt, go for plain full-fat yogurt for the closest texture. It keeps the dough creamy and works well in a pinch.

4-Step 4: Mix in the dry ingredients Add 3 cups flour, 1 tsp baking powder, 1 tsp cornstarch, and 1/2 tsp salt. Stir just until the dough comes together. Once the flour goes in, you want to avoid overmixing because that can make the cookies tougher than they should be. The dough should be soft but scoopable. If it feels sticky, let it rest for a few minutes before shaping.

5-Step 5: Make the brown sugar topping In a separate bowl, combine 1/2 cup melted butter and 1 cup packed light brown sugar. This mixture becomes the glossy, candy-like layer under the pineapple. Spoon about 1 tablespoon of the brown sugar mixture into each cavity and spread it evenly across the bottom. Next, top each section with 1 pineapple slice and place 1 maraschino cherry in the center. This is the part where the cookies start looking like little mini cakes in disguise.

6-Step 6: Add the cookie dough Scoop about 3 tablespoons cookie dough into each cavity. Flatten the dough gently with an offset spatula so it covers the topping without pressing too hard. The dough should sit nicely over the pineapple and cherry, kind of like a cozy blanket with dessert ambitions. If the recipe gives you a few extra cookies, that is not a problem. Recipe yield can vary a bit depending on how generously you scoop.

7-Step 7: Bake until golden Bake for 25 minutes, or until the edges are golden and the brown sugar is bubbling around the sides. The tops should look set, not wet, and the kitchen will smell like butter, pineapple, and sugar doing a happy little dance. Watch the color more than the clock if your oven runs hot or cool. A few extra minutes can make the difference between soft and dry, so keep an eye on them near the end.

8-Step 8: Cool and invert carefully Let the cookies cool for 10 minutes after baking. This short rest helps the topping settle so the cookies do not fall apart when you flip them. Then invert them onto a surface lined with wax paper to catch the sticky brown sugar drips. If a pineapple slice sticks, gently reposition it with a spatula. Don’t panic if one cookie looks a little messy. Honestly, the imperfect ones are often the first to disappear.

9-Step 9: Finish cooling before serving Let the cookies cool completely before serving. This helps the topping firm up a bit and makes the cookies easier to pick up. Store them in an airtight container once they are cool.