Name: Pineapple Upside Sugar Cookies
Prep time: 20 min
Cook time: 14 min
Total time: 1 h
Cuisine: American
Ingredients: 2 1/4 cups all-purpose flour; 1/2 teaspoon baking powder; 1/4 teaspoon salt; 1 cup unsalted butter, softened; 3/4 cup granulated sugar; 1 large egg; 1 teaspoon vanilla extract; 6 canned pineapple rings, cut into small chunks; 12 maraschino cherries, halved; 1/2 cup light brown sugar

These Pineapple Upside Sugar Cookies are a tropical twist on the classic sugar cookie. With a caramelized pineapple topping and a cherry in the center, they bring all the flavors of a pineapple upside-down cake in a perfectly portioned, hand-held treat. Soft, buttery, and lightly golden around the edges, these cookies are ideal for sunny gatherings, festive holidays, or when I want to treat myself to something a little bit different. Pineapple Upside Sugar Cookies

Why You’ll Love This Recipe

I love how this recipe captures the nostalgia of pineapple upside-down cake while being quick and simple like a batch of cookies. There’s no need for slicing a cake or worrying about presentation — each cookie is already beautifully decorated with golden pineapple and a bright cherry. The brown sugar caramel topping adds that gooey sweetness I crave, and the sugar cookie base is soft but holds up well to the topping. It’s a fun and fruity upgrade to my usual cookie routine.

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, softened
Granulated sugar
Egg
Vanilla extract
Canned pineapple rings (cut into small chunks or pieces)
Maraschino cherries
Light brown sugar

directions

I preheat the oven to 350°F (175°C) and line a baking sheet with parchment paper.
In a bowl, I whisk together the flour, baking powder, and salt.
In another bowl, I cream the butter and granulated sugar until light and fluffy.
I beat in the egg and vanilla extract until well combined.
I gradually mix the dry ingredients into the wet ingredients to form a soft dough.
I scoop portions of dough onto the baking sheet, spacing them a couple of inches apart.
I press a small pile of brown sugar in the center of each cookie, then top it with a piece of pineapple and half a maraschino cherry.
I bake the cookies for about 12-14 minutes, until the edges are lightly golden and the sugar has caramelized.
After baking, I let the cookies cool on the baking sheet for a few minutes before transferring them to a wire rack.

Servings and timing

This recipe makes about 24 cookies. I usually spend around 20 minutes preparing the dough and toppings, and baking takes another 12 to 14 minutes per batch. Altogether, I can have everything done and cooled within 45 minutes to 1 hour.

Variations

Sometimes I swap the sugar cookie base for a shortbread-style dough for a crumblier texture. If I want extra flavor, I add a splash of pineapple juice to the dough or a bit of coconut extract for a piña colada vibe. When I’m feeling festive, I drizzle a bit of white chocolate over the cooled cookies for added sweetness and decoration.

storage/reheating

I store these cookies in an airtight container at room temperature for up to 3 days. If I want to keep them longer, I refrigerate them for up to a week. They also freeze well — I just make sure they’re fully cooled and place them between layers of parchment paper before freezing. To reheat, I warm them slightly in the microwave for 10-15 seconds to bring back a bit of that soft, gooey texture.

FAQs

How do I keep the pineapple from making the cookies soggy?

I pat the pineapple pieces dry with a paper towel before adding them to the cookies. This helps prevent excess moisture from soaking into the dough.

Can I use fresh pineapple instead of canned?

Yes, I can use fresh pineapple as long as I cut it into small, even pieces and make sure it’s not too juicy. It adds a brighter, tangier flavor.

Do I need to chill the dough?

I don’t usually chill this dough, but if the butter is very soft or it’s a hot day, I might chill it for 15-20 minutes so the cookies don’t spread too much.

Can I make these cookies ahead of time?

Absolutely. I often make the dough ahead of time and refrigerate it overnight. I assemble and bake the cookies just before serving for the best texture.

What if I don’t have maraschino cherries?

I’ve used dried cherries or even a small dollop of raspberry jam as a substitute. The pop of color and sweet-tart flavor still work well with the pineapple.

Conclusion

Pineapple Upside Sugar Cookies bring a sunny, nostalgic twist to my cookie baking. They’re quick to make, cheerful to serve, and full of buttery, fruity flavor. Whether I’m baking for a party or just because, this recipe always brightens the day.