Name: Pineapple Upside Sugar Cookies
Prep time: 20 min
Cook time: 14 min
Total time: 35 min
Cuisine: American
Ingredients: 2 cups all-purpose flour; 1 tsp baking powder; 1/4 tsp salt; 3/4 cup unsalted butter, softened; 1 cup granulated sugar; 1 large egg; 1 tsp vanilla extract; 1/2 cup crushed pineapple, drained well; 10 maraschino cherries, halved; 1/2 cup brown sugar

These Pineapple Upside Sugar Cookies take a fun tropical twist on the classic upside-down cake. They feature buttery sugar cookie dough topped with caramelized pineapple and maraschino cherries for a nostalgic and fruity dessert that’s both simple and crowd-pleasing.

Why You’ll Love This Recipe

I love how these cookies combine the sweetness and buttery texture of a sugar cookie with the sticky, golden top of a pineapple upside-down cake. Each bite delivers tropical flavor with a gooey, caramelized finish. They’re perfect for potlucks, family gatherings, or when I want a dessert that’s both comforting and slightly out of the ordinary. Plus, the individual cookie format makes serving a breeze.

Ingredients

(Here’s a tip: Check out the full list of ingredients and measurements in the recipe card below.)

All-purpose flour
Baking powder
Salt
Unsalted butter
Granulated sugar
Egg
Vanilla extract
Crushed pineapple (drained well)
Maraschino cherries
Brown sugar

Directions

I start by preheating the oven to 350°F and lining my baking sheet with parchment paper.
I mix the dry ingredients: flour, baking powder, and salt in a bowl.
In a separate bowl, I cream together the butter and granulated sugar until fluffy. Then I add in the egg and vanilla extract, mixing until combined.
I gradually add the dry ingredients to the wet, mixing until a soft dough forms.
On the baking sheet, I place small mounds of brown sugar, followed by a spoonful of crushed pineapple and a half cherry in the center.
I scoop cookie dough over each pineapple mound, pressing lightly to cover.
I bake for 12–14 minutes, until the edges are lightly golden.
Once out of the oven, I let them cool slightly before flipping them over to reveal the caramelized pineapple top.

Servings and timing

This recipe makes about 20 cookies.
Prep time: 20 minutes
Bake time: 12–14 minutes
Total time: around 35 minutes

Variations

When I want a twist, I sometimes mix a bit of coconut into the dough for a more tropical flavor. Swapping brown sugar for dark brown sugar gives a richer caramelization. For a more buttery base, I’ve also tried brushing the parchment with melted butter before adding the brown sugar and pineapple.

Storage/Reheating

I store these cookies in an airtight container at room temperature for up to 3 days. If they need softening, a quick 5–8 seconds in the microwave does the trick. For longer storage, I freeze them in layers with parchment paper between for up to 2 months and reheat gently in the oven at 300°F for 5–7 minutes.

FAQs

What kind of pineapple works best for these cookies?

I always use crushed pineapple that’s been well-drained to avoid soggy cookies. If I use pineapple rings, I chop them finely for even distribution.

Do I need to flip the cookies while they’re still hot?

Yes, flipping them while warm is key. That way the caramelized fruit topping comes off cleanly and sets nicely on top of the cookie.

Can I use canned pineapple chunks instead?

I can, but I make sure to chop them finely and drain the juice really well to prevent excess moisture.

Do I have to use parchment paper?

I highly recommend it. Parchment helps prevent sticking, especially with the caramelized sugar and fruit.

Are these cookies good for gifting?

Absolutely! They look beautiful and taste even better. I sometimes wrap them individually in cellophane for a homemade treat that travels well.

Conclusion

These Pineapple Upside Sugar Cookies are my go-to when I crave a fruity, buttery dessert with a nostalgic twist. They’re simple to make, stunning to look at, and full of vibrant tropical flavor. Whether for a summer party or a sweet treat any time of year, these cookies never disappoint.