You know that feeling when you want a pineapple upside-down cake, but you don’t really want to make a whole entire cake? Yeah, me too. It’s a lot of work for something that you might just want a little piece of.
That’s where these cookies come in. They have all the good parts of the cake—the gooey brown sugar, the sweet pineapple, that perfect cherry—but in a soft, chewy sugar cookie. I’m going to show you exactly how to make them, and I promise it’s way easier than you think. You’ll get perfect little mini cakes that look amazing and taste even better.
What You’ll Need
Breaking this down is simple. You have the stuff for the topping, which is the gooey, amazing part, and then you have the stuff for the actual cookie. Don’t let the list scare you; most of this is probably already in your kitchen.
First up, let’s talk about the topping. This is what creates that classic caramelized pineapple flavor at the bottom of the muffin tin, which becomes the top of the cookie.
Topping Ingredients
| Ingredient | Amount |
|---|---|
| Unsalted Butter | ½ cup (1 stick) |
| Light Brown Sugar | 1 cup, packed |
| Canned Pineapple Slices | 1 can (20 oz) |
| Maraschino Cherries | 12 cherries |
Now for the cookie part. This is a super soft, reliable sugar cookie base that holds up to the topping without getting soggy. It’s buttery and has just the right amount of sweetness to balance the pineapple.
Cookie Dough Ingredients
| Ingredient | Amount |
|---|---|
| All-Purpose Flour | 2 ¾ cups |
| Baking Soda | 1 tsp |
| Baking Powder | ½ tsp |
| Salt | ½ tsp |
| Unsalted Butter | 1 cup (2 sticks), softened |
| Granulated Sugar | 1 cup |
| Egg | 1 large |
| Vanilla Extract | 2 tsp |
Tools You’ll Need
You don’t need a bunch of fancy gadgets for this. A standard muffin tin is the most important piece of equipment. It acts like a little mini cake pan for each cookie.
| Tool | Purpose |
|---|---|
| Standard Muffin Tin | Shaping the cookies |
| Mixing Bowls | For wet & dry ingredients |
| Hand or Stand Mixer | Creaming butter & sugar |
| Whisk | Combining dry ingredients |
| Spatula | Scraping the bowl |
| Cookie Scoop | Uniform dough balls |
| Wire Rack | Cooling the cookies |
Pro Tips from My Kitchen
I’ve made these cookies more times than I can count, and I’ve learned a few things that make a huge difference. These aren’t just suggestions; they are the keys to getting it right every single time.
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Don’t Overfill the Muffin Cups. It’s so tempting to pack in the brown sugar mixture and a huge scoop of dough. Trust me, don’t do it. A tablespoon of the sugar mixture and a medium cookie scoop of dough is plenty. If you add too much, the topping will bubble over and make a sticky mess in your oven, and the cookie will bake unevenly.
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The Flip is Time-Sensitive. This is the most important step. You have to flip the pan over onto a baking sheet or cooling rack while the cookies are still warm. Let them cool in the pan for about 5-7 minutes—no longer. If you wait until they’re completely cool, that beautiful brown sugar topping will turn into candy cement and your cookies will be stuck forever. A warm flip lets them slide right out.
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Room Temperature Ingredients Matter. I know, I know, every recipe says this. But for this one, it’s critical. Softened butter and a room temperature egg mix together to create a smooth, emulsified batter. This gives you a tender, chewy cookie instead of a dense, tough one. Cold ingredients don’t mix well and can make your dough lumpy. Just leave the butter and egg on the counter for about an hour before you start.
Let’s Make Some Pineapple Upside-Down Cookies
Alright, let’s get into it. We’ll do this in two main parts: making the topping and then making the cookie dough.
Part 1: The Topping
Step 1: First, preheat your oven to 375°F (190°C). Then, grab your standard 12-cup muffin tin. You don’t need to grease it, since we’re basically lining it with butter and sugar.
Step 2: Melt your ½ cup of butter in a small saucepan or in the microwave. Once it’s melted, stir in the 1 cup of packed light brown sugar until it’s all combined. It will look like a grainy, wet sand.
Step 3: Spoon about one tablespoon of this buttery sugar mixture into the bottom of each muffin cup. Use the back of the spoon to spread it out into an even layer. This is your caramel base.
Step 4: Now for the pineapple. Drain the can of pineapple slices really well. You can even pat them with a paper towel to get rid of extra juice. Place one pineapple slice on top of the sugar mixture in each cup. (If your slices are big, you might need to trim them a bit to fit).
Step 5: Place one maraschino cherry right in the center of each pineapple ring. Your base is now ready for the cookie dough. Set the muffin tin aside for a minute.
Part 2: The Sugar Cookie Dough
Step 1: In a medium bowl, whisk together your dry ingredients: the 2 ¾ cups of flour, 1 teaspoon of baking soda, ½ teaspoon of baking powder, and ½ teaspoon of salt. This just makes sure everything is evenly mixed before it goes into the wet stuff.
Step 2: In a separate, larger bowl, use a hand mixer or stand mixer to beat the 1 cup of softened butter and 1 cup of granulated sugar together. Cream them on medium-high speed for about 2-3 minutes until the mixture is light, pale, and fluffy.
Step 3: Add the large egg and the 2 teaspoons of vanilla extract to the butter mixture. Beat again on medium speed for another minute until everything is well combined. Remember to scrape down the sides of the bowl with a spatula so you get all the good stuff.
Step 4: With the mixer on low speed, slowly add the dry ingredient mixture to the wet ingredients. Mix just until the flour is incorporated. (Don’t overmix here, or you’ll get tough cookies). The dough will be thick and a little sticky.
Part 3: Assembly and Baking
Step 1: Grab a medium cookie scoop (about 1.5 tablespoons) and scoop out balls of dough. Place one scoop of dough directly on top of the cherry and pineapple in each muffin cup. You don’t need to press it down; the dough will spread out as it bakes.
Step 2: Place the muffin tin in the preheated oven and bake for 12-15 minutes. You’ll know they’re done when the edges of the cookies are a light golden brown and the center looks set.
Step 3: This next part is important. Take the pan out of the oven and let it cool on a wire rack for exactly 5 minutes. Set a timer. This lets the cookies set up just enough without letting the caramel topping harden.
Step 4: After 5 minutes, place a large baking sheet or a wire rack over the top of the muffin tin. Carefully and quickly, flip the whole thing over. The cookies should drop right out onto the sheet. If any topping gets left behind in the pan, just use a spoon to scoop it out and put it back on the cookies while it’s still warm.
Substitutions and Fun Variations
One of the best things about this recipe is how you can change it up. Think of it as a starting point.
- Different Fruit: Not a pineapple fan? Try this with canned, drained peach slices or even mandarin oranges. You could even use sliced apples with a sprinkle of cinnamon in the brown sugar mixture for a fall version.
- Go Nuts: Add some chopped pecans or walnuts to the brown sugar mixture before adding the pineapple. It gives the cookies a nice crunchy texture.
- Spice it Up: Add ½ teaspoon of cinnamon or a ¼ teaspoon of nutmeg to your dry ingredients for the cookie dough. It adds a nice warmth that goes really well with the brown sugar and pineapple.
- Gluten-Free Option: You can substitute the all-purpose flour with a good quality 1-to-1 gluten-free baking flour blend. I’ve had good results with Bob’s Red Mill 1-to-1.
Make-Ahead and Storage Tips
Life gets busy, so it’s good to know what you can prep ahead of time.
Make-Ahead: The cookie dough is perfect for making in advance. You can make the dough, cover the bowl tightly with plastic wrap, and store it in the refrigerator for up to 3 days. When you’re ready to bake, just let it sit out for about 15 minutes to soften slightly before scooping.
Storage: Once the cookies are completely cool, you can store them in a single layer in an airtight container at room temperature. They’ll stay soft and delicious for about 3 to 4 days. I don’t recommend stacking them, because the topping is sticky and they’ll all glue together into one giant cookie blob.
Frequently Asked Questions
Q1. My cookies are stuck in the pan! What did I do wrong?
Ans: You probably let them cool for too long. Just pop the whole pan back into the warm oven for a minute or two to re-melt the caramel, then try flipping it again.
Q2. Can I use a mini muffin tin instead?
Ans: You can, but you’ll need to adjust everything. Use crushed pineapple instead of slices and reduce the baking time to about 8-10 minutes. They make great little bite-sized treats.
Q3. Do I have to use canned pineapple?
Ans: Canned works best because it has a consistent sweetness and moisture level. If you want to use fresh pineapple, make sure you slice it very thin and pat it very, very dry with paper towels to remove as much juice as possible.
Q4. My cookie dough seems really soft and sticky. Is that normal?
Ans: Yes, it is a soft dough. That’s what makes the final cookie so tender. A cookie scoop is your best friend here because it makes handling the sticky dough much easier.
Wrapping Up
See? You just made something that looks super fancy but was actually pretty simple. These cookies are a huge hit whenever I make them, and they disappear fast. They’re perfect for bringing to a party, a potluck, or just for treating yourself when you want that pineapple upside-down cake flavor without all the fuss.
Now it’s your turn. Give this recipe a try and see for yourself. I’d love to hear how it goes, so drop a comment below and tell me what you think. And if you have any questions along the way, just ask