Name: Pineapple Upside-Down Sugar Cookies
Prep time: 15 min
Cook time: 15 min
Total time: 30 min
Cuisine: American
Ingredients: 1/2 cup unsalted butter, softened; 3/4 cup granulated sugar; 1 large egg; 1 teaspoon vanilla extract; 1 1/2 cups all-purpose flour; 1/2 teaspoon baking powder; 1/4 teaspoon salt; 1/2 cup packed brown sugar; 6 pineapple rings, cut into small pieces; 6 maraschino cherries, halved; 1 tablespoon reserved pineapple juice

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I love turning classic desserts into fun, handheld treats, and these Pineapple Upside-Down Sugar Cookies are exactly that. I combine soft, buttery sugar cookie dough with caramelized brown sugar, juicy pineapple pieces, and bright cherry centers to create a tropical-inspired dessert that feels both nostalgic and fresh.

Pineapple Upside-Down Sugar Cookies

Ingredients

(Tip: You'll find the full list of ingredients and measurements in the recipe card below.)

½ cup unsalted butter, softened

¾ cup granulated sugar

1 large egg

1 teaspoon vanilla extract

1 ½ cups all-purpose flour

½ teaspoon baking powder

¼ teaspoon salt

½ cup packed brown sugar

6 pineapple rings, cut into small pieces

maraschino cherries, halved (about 6 cherries)

1 tablespoon reserved pineapple juice

Directions

I start by preheating the oven to 350°F (175°C) and lightly greasing a muffin tin or lining it with parchment baking cups.

In a small bowl, I sprinkle about 1 teaspoon of brown sugar into the bottom of each muffin cavity. I add a few small pineapple pieces and place half a cherry in the center. I drizzle a few drops of pineapple juice over each cavity to help create that caramelized topping.

In a large mixing bowl, I cream the butter and granulated sugar until the mixture is light and fluffy. I beat in the egg and vanilla extract until everything is well combined.

In a separate bowl, I whisk together the flour, baking powder, and salt. I gradually add the dry ingredients to the wet mixture, stirring until a soft dough forms.

I scoop about 1 tablespoon of dough and gently press it over the pineapple mixture in each muffin cavity, smoothing the tops so they are even.

I bake the cookies for 12 to 15 minutes, or until the edges are lightly golden.

Once baked, I allow the cookies to cool in the pan for about 5 minutes. Then I carefully invert them onto a baking sheet or tray to release. I let them cool completely before serving.

Servings and timing

Prep Time: 15 minutes

Cooking Time: 15 minutes

Total Time: 30 minutes

Servings: 12 cookies

Calories: approximately 180 kcal per cookie

Variations

I sometimes swap the pineapple for small mango pieces for a different tropical flavor.

I like adding a pinch of cinnamon to the brown sugar layer for a warm, spiced touch.

When I want extra texture, I sprinkle a few chopped pecans or shredded coconut into the bottom of each muffin cavity before adding the dough.

I also experiment with almond extract instead of vanilla for a slightly nutty flavor twist.

Storage/Reheating

I store these cookies in an airtight container at room temperature for up to 3 days. If I want them to last longer, I keep them in the refrigerator for up to 5 days.

To serve them warm, I microwave a cookie for about 8–10 seconds. This helps soften the caramelized topping and brings back that fresh-from-the-oven texture.

If I plan to freeze them, I place the cooled cookies in a single layer in an airtight container and freeze for up to 2 months. I thaw them at room temperature before serving.

FAQs

Can I use canned pineapple for this recipe?

I use canned pineapple rings most often, and I make sure to drain them well. I like reserving a little of the juice for drizzling over the brown sugar layer.

Do I have to use a muffin tin?

I prefer using a muffin tin because it helps create the classic upside-down look. If I do not have one, I use silicone muffin molds to achieve a similar result.

How do I prevent the cookies from sticking?

I lightly grease the pan or use parchment baking cups. I also let the cookies cool for about 5 minutes before inverting, which helps them release more easily.

Can I make the dough ahead of time?

I sometimes prepare the dough a day in advance and store it covered in the refrigerator. I let it sit at room temperature for about 10 minutes before scooping and assembling.

Why are my cookies too soft in the center?

I check that I bake them until the edges are lightly golden. If they seem too soft, I add 1–2 extra minutes of baking time, keeping a close eye to avoid overbaking.

Conclusion

I find these Pineapple Upside-Down Sugar Cookies to be a delightful twist on a classic dessert. I love how the caramelized pineapple and cherry topping pairs with the soft, buttery cookie base. They are easy to prepare, visually charming, and always a hit whenever I share them. Whether I make them for a gathering or just to satisfy a sweet craving, they never disappoint.

📖 Recipe:

Pineapple Upside-Down Sugar Cookies

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Author: Cheryl
Total Time: 30 minutes
Yield: 12 cookies
Diet: Vegetarian

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Description

These Pineapple Upside-Down Sugar Cookies combine soft, buttery sugar cookie dough with caramelized brown sugar, juicy pineapple pieces, and bright cherry centers for a fun, handheld twist on the classic cake.

Instructions

Preheat the oven to 350°F (175°C) and lightly grease a muffin tin or line with parchment baking cups.
Sprinkle about 1 teaspoon of brown sugar into the bottom of each muffin cavity. Add a few pineapple pieces and place half a cherry in the center. Drizzle a few drops of pineapple juice over each.
In a large bowl, cream the butter and granulated sugar until light and fluffy. Beat in the egg and vanilla extract until well combined.
In a separate bowl, whisk together the flour, baking powder, and salt. Gradually add the dry ingredients to the wet mixture and mix until a soft dough forms.
Scoop about 1 tablespoon of dough and gently press it over the pineapple mixture in each muffin cavity, smoothing the tops evenly.
Bake for 12 to 15 minutes, or until the edges are lightly golden.
Cool in the pan for 5 minutes, then carefully invert onto a tray to release. Let cool completely before serving.