Pineapple upside sugar cookies are a fun, tropical twist on the classic pineapple upside-down cake. With buttery sugar cookie dough as the base and a caramelized pineapple-cherry topping baked right in, these cookies are like little bites of sunshine. I love making them when I want something unique, fruity, and nostalgic—all in one bite-sized treat.
Why You’ll Love This Recipe
I love how these cookies combine the soft, chewy texture of sugar cookies with the gooey, caramelized top of a pineapple upside-down cake. They’re adorable, super flavorful, and easier to make than a full cake. Plus, they bring a pop of color and sweetness to any dessert spread or party tray. They’re a guaranteed conversation starter—and crowd-pleaser.
Ingredients
(Here's a tip: Check out the full list of ingredients and measurements in the recipe card below.)
- Unsalted butter, softened
- Granulated sugar
- Egg
- Vanilla extract
- All-purpose flour
- Baking powder
- Salt
- Pineapple rings (cut into small pieces)
- Maraschino cherries (halved)
- Brown sugar
- Optional: a little pineapple juice for added flavor in the dough
Directions
- I start by preheating the oven to 350°F (175°C) and lightly greasing a muffin tin.
- I place a bit of brown sugar in the bottom of each muffin cup, then add a small piece of pineapple and half a maraschino cherry, cut-side down.
- In a bowl, I cream the butter and sugar until light and fluffy, then beat in the egg and vanilla.
- I mix in the flour, baking powder, and salt until a soft dough forms. If I want extra pineapple flavor, I add a teaspoon or two of pineapple juice.
- I scoop a ball of dough and press it gently over the fruit in each muffin cup. I try to cover the fruit evenly without packing it in too tightly.
- I bake the cookies for 12–15 minutes, until the edges are lightly golden and the centers are set.
- After baking, I let them cool in the pan for 5 minutes, then carefully invert the pan onto a tray to release the cookies—just like turning out an upside-down cake.
- I let them cool completely before serving.
Servings and Timing
This recipe makes about 12 cookies. It takes around 15 minutes to prep and 12–15 minutes to bake, so the total time is just about 30 minutes.
Variations
I like to add a touch of coconut extract to the dough for extra island flavor. Sometimes I sprinkle shredded coconut into the muffin cups for a toasty base. For a shortcut, I’ve also made these using store-bought sugar cookie dough—just mix in a little vanilla or pineapple juice to give it a homemade taste.
Storage/Reheating
I keep these cookies in an airtight container at room temperature for up to 3 days or in the fridge for up to a week. To reheat, I pop them in the microwave for 10–15 seconds to soften them up and bring out the caramelized flavor again. They’re also great straight from the fridge.
FAQs
Can I use canned pineapple?
Yes, I always use canned pineapple rings for convenience. I just pat them dry before using so the cookies don’t get soggy.
What if I don’t have a muffin tin?
I’ve used mini tart pans or ramekins before, but muffin tins work best to shape the cookies and keep the topping in place.
Can I make the dough ahead of time?
Absolutely. I often make the dough a day ahead and keep it in the fridge. It actually makes shaping easier when the dough is slightly chilled.
Do these cookies need to be refrigerated?
Not necessarily, but I find they last longer and stay moist if I keep them in the fridge, especially if I’m storing them more than a couple of days.
Can I freeze these cookies?
Yes, once they’re cooled, I freeze them in a single layer first, then stack them with parchment between layers in a container. They thaw quickly and taste just as good.
Conclusion
Pineapple upside sugar cookies are the perfect mash-up of two dessert favorites—sweet, chewy sugar cookies and fruity, caramelized upside-down cake. They’re eye-catching, easy to make, and packed with tropical flavor. Whether I’m baking for a summer party or just want to brighten up my week, these cookies always bring the sunshine.
Pineapple Upside Sugar Cookies
- Prep Time: 15 minutes
- Cook Time: 15 minutes
- Total Time: 30 minutes
- Yield: 12 cookies
- Category: Dessert
- Method: Baking
- Cuisine: American
- Diet: Vegetarian
Description
These pineapple upside sugar cookies combine the fruity, caramelized magic of pineapple upside-down cake with the soft, chewy goodness of a sugar cookie. With bright pineapple, maraschino cherries, and a buttery base, these bite-sized treats are tropical, nostalgic, and guaranteed to impress.
Ingredients
- ½ cup unsalted butter, softened
- ¾ cup granulated sugar
- 1 egg
- 1 tsp vanilla extract
- 1 ¼ cups all-purpose flour
- ½ tsp baking powder
- ¼ tsp salt
- 6 canned pineapple rings, cut into small chunks
- 6 maraschino cherries, halved
- ¼ cup brown sugar
- Optional: 1–2 teaspoon pineapple juice (for extra flavor)
Instructions
- Preheat oven to 350°F (175°C). Lightly grease a standard muffin tin.
- Place 1 teaspoon brown sugar into the bottom of each muffin cup. Add a pineapple chunk and a cherry half, cut-side down.
- In a bowl, cream the butter and granulated sugar until light and fluffy.
- Beat in the egg and vanilla extract. Add pineapple juice if using.
- In a separate bowl, whisk together flour, baking powder, and salt. Gradually add to the wet ingredients to form a soft dough.
- Scoop and gently press dough over the fruit in each muffin cup, covering evenly.
- Bake for 12–15 minutes, until edges are golden and centers are set.
- Let cool in the pan for 5 minutes, then invert onto a tray to release the cookies.
- Cool completely before serving.
Notes
- Pat pineapple chunks dry before using to avoid soggy cookies.
- Add coconut extract or shredded coconut for a tropical twist.
- Store-bought sugar cookie dough works in a pinch—just enhance it with vanilla or pineapple juice.
- Dough can be made ahead and refrigerated for easier shaping.
