Classic cake, fun cookie twist
These pineapple upside down sugar cookies turn the classic retro cake into a soft, chewy, bite-sized treat that’s impossible to resist. With a caramelized brown sugar base, sweet pineapple, and a bright cherry center, every cookie delivers that nostalgic tropical flavor—without the fuss of baking a whole cake. They’re perfect for parties, potlucks, holidays, or whenever you want a dessert that looks impressive but is surprisingly easy to make. Best of all, these cookies come together quickly, making them ideal for busy bakers who still want something fun, pretty, and totally pin-worthy. 🍍🍒
⏱️ Time Breakdown
- Prep Time: 20 minutes
- Cook Time: 12–14 minutes
- Total Time: 35 minutes
- Servings: 20–22 cookies
📝 Ingredients List
For the Topping
- ¼ cup unsalted butter, melted
- ½ cup brown sugar, packed
- ½ cup canned pineapple tidbits, well-drained
- 10–11 maraschino cherries, halved
For the Sugar Cookies
- 2¼ cups all-purpose flour
- ½ tsp baking powder
- ¼ tsp salt
- ¾ cup unsalted butter, softened
- ¾ cup granulated sugar
- 1 large egg, room temperature
- 1½ tsp vanilla extract
✨ Kitchen Tools You’ll Need
This recipe doesn’t require fancy gadgets, just a few reliable kitchen basics to keep everything simple and stress-free.
- Muffin tin (standard size)
- Mixing bowls
- Electric mixer or whisk
- Measuring cups & spoons
- Rubber spatula
- Cooling rack
👩🍳 Step-by-Step Beginner-Friendly Instructions
- Preheat & prep: Preheat oven to 350°F (175°C). Grease a muffin tin generously.
- Make the topping: Spoon about 1 teaspoon melted butter into each muffin cup. Sprinkle 1 tablespoon brown sugar over the butter.
- Add fruit: Place pineapple tidbits evenly over the sugar, then press a cherry half into the center. 🍍🍒
- Mix dry ingredients: In a bowl, whisk flour, baking powder, and salt together.
- Cream butter & sugar: Beat butter and granulated sugar for 2 minutes until light and fluffy.
- Add egg & vanilla: Mix in egg and vanilla until smooth.
- Combine: Gradually add dry ingredients, mixing just until dough forms.
- Assemble: Scoop about 2 tablespoons of dough and gently flatten over the fruit in each cup.
- Bake: Bake for 12–14 minutes, until edges are lightly golden.
- Flip carefully: Cool for 5 minutes, then invert onto a tray or rack while warm. ✨
💡 Pro Tips
- Drain well: Excess pineapple juice can make cookies soggy—pat fruit dry with paper towels.
- Clean flip: Loosen edges gently with a butter knife before flipping for perfect tops.
- Storage: Store in an airtight container at room temperature for 2 days or refrigerate up to 5 days.
- Mini version: Use a mini muffin pan and bake 9–10 minutes for bite-sized treats.