When I first made Pineapple Upside Sugar Cookies, it was a happy accident born from leftover pineapple and a craving for something nostalgic yet new. They immediately reminded me of pineapple upside-down cake, but with the simplicity and buttery goodness of a sugar cookie. Every bite is a little tropical getaway—sweet pineapple caramelized with brown sugar nestled into soft, chewy cookie dough.

These cookies are a conversation starter, a twist on tradition, and an easy way to bring sunshine to your dessert table any time of year. Whether you bake them in a mini muffin tin or flat on a sheet, the result is equally delightful!

Why You’ll Love This Recipe

Tropical Flavor: Bright pineapple and brown sugar create a luscious, juicy topping.
Soft and Buttery: The sugar cookie base is tender and flavorful.
Easy to Make: Simple ingredients, no mixer required.
Mini or Classic Options: Make them like thumbprint cookies or mini upside-down cakes.
Great for Sharing: Perfect for parties, potlucks, and gifting.
Kid-Friendly Fun: Little hands love helping with the topping and pressing the dough.

Ingredients You’ll Need

For the Pineapple Topping:

1 cup crushed pineapple, drained (reserve the juice)
1/4 cup packed brown sugar
1 tablespoon unsalted butter, melted

For the Cookie Dough:

1 cup unsalted butter, softened
1 cup granulated sugar
1 large egg
1 teaspoon vanilla extract
2 cups all-purpose flour
1/2 teaspoon baking powder
1/4 teaspoon salt
2–3 tablespoons reserved pineapple juice

Substitution Tips:

Use canned pineapple tidbits finely chopped if crushed isn’t available.
Margarine can replace butter in a pinch, but flavor may vary.

Step-by-Step Instructions

Preheat and Prep

Preheat oven to 350°F (175°C). Grease a mini muffin tin or line a baking sheet with parchment paper. Tip: Use nonstick spray even in nonstick pans to ensure easy release.

Make the Pineapple Topping

In a small bowl, mix the drained pineapple, brown sugar, and melted butter. Tip: Drain pineapple thoroughly to avoid soggy cookies.

Make the Dough

In a large bowl, cream the softened butter and granulated sugar until light and fluffy. Beat in the egg and vanilla extract until smooth. In a separate bowl, whisk together flour, baking powder, and salt. Gradually add the dry ingredients to the butter mixture. Stir in 2–3 tablespoons of reserved pineapple juice to soften the dough. Tip: Chill the dough for 20 minutes if it feels too soft to scoop.

Assemble

For mini muffin tin version: Spoon about 1 teaspoon of the pineapple topping into each cup. Add a tablespoon of cookie dough on top and press gently.

For cookie sheet version: Drop dough by tablespoon, make a thumbprint in each, and fill the well with a bit of pineapple topping.

Bake

Bake for 12–14 minutes, or until edges are golden. Let cool in the pan for 5 minutes, then transfer to a wire rack. Tip: If using a muffin tin, run a knife around each cookie to release.

Serving and Storage Tips

Serve warm for a gooey center or chill for a firmer bite. Delicious with a scoop of vanilla ice cream or alongside a tropical fruit salad.

Store in an airtight container at room temperature for 3 days or refrigerate for up to a week. Freeze cookies for up to 2 months in a single layer with parchment between layers.

Helpful Notes

Drain Pineapple Well: Extra liquid will make cookies soggy.
Chill Dough If Needed: Helps hold shape during baking.
Creative Shapes: Use silicone molds for fun party-ready shapes.
Flavor Twist: Add a pinch of cinnamon or a dash of coconut extract for extra depth.

Frequently Asked Questions

Can I use fresh pineapple?
Yes, just finely chop and drain well before using.
What if I don’t have a mini muffin tin?
Use a baking sheet and make thumbprint-style cookies instead.
Why did my cookies spread too much?
The dough may have been too warm; chilling helps prevent spreading.
Can I make these ahead of time?
Yes, bake and freeze them, or prepare the dough and topping in advance.
Can I double the recipe?
Absolutely! Great for big gatherings or holiday baking.
What other fruits can I use?
Try finely chopped peaches, mango, or canned cherries.

Final Thoughts

Pineapple Upside Sugar Cookies are a cheerful twist on two classics, bringing the sunny sweetness of pineapple upside-down cake into the world of handheld treats. They’re simple to make, fun to share, and guaranteed to brighten your cookie tray.

Tried them out? I’d love to hear your favorite way to shape or serve these sweet bites!