I love bright, simple treats and this Pineapple Upside Down Sugar Cookies , is a sunny twist I make often. These cookies taste like a small cake and they bring a sweet, fruity pop to any plate, day or night. If you love upside-down desserts, check my ultimate guide to cranberry pineapple upside-down cake for more ideas.
I first made these when Dad James asked for something fun with canned pineapple; he smiled at the first bite and asked for more the next day.
What You’ll Need
- 1 cup unsalted butter (softened)
- 1 cup granulated sugar
- 1 large egg
- 1 teaspoon vanilla extract (optional)
- 2 cups all-purpose flour (or gluten-free blend)
- 1 teaspoon baking soda
- 1/2 teaspoon salt
- 1 can canned pineapple rings (well-drained)
- 2 tablespoons additional sugar for sprinkling
My Trusted Kitchen Tools
I keep the tools simple: a mixing bowl, hand mixer or stand mixer, cookie scoop, baking sheet, and a wire rack. If you like dough ideas and test recipes, you can see a fun twist in my brown sugar pop tart cookies post.
Bringing It All Together
- Preheat the oven to 350°F (175°C).
- Cream the butter and 1 cup sugar until light.
- Beat in the egg and vanilla until smooth.
- Whisk the flour, baking soda, and salt in a bowl.
- Stir the dry mix into the wet mix until a soft dough forms.
- Scoop dough into small balls and place on a baking sheet.
- Flatten each ball slightly and set one pineapple ring on top.
- Sprinkle each ring with a little of the 2 tablespoons sugar.
- Bake until edges are set, about 10 to 12 minutes.
- Let cool on the baking sheet for 5 minutes, then move to a rack to cool fully.
Making It Your Own (Swaps & Ideas)
You can swap canned pineapple for crushed pineapple for a softer top or add a maraschino cherry in the center for color. Try brown sugar in place of some white sugar for a deeper taste. For a richer dessert idea, see my take on the chocolate cherry upside-down cake for flavor hints.
How We Love to Serve It
I serve these warm or at room temp. They pair well with a scoop of vanilla ice cream or a light cup of tea. They work as a dessert or a sweet snack for guests.
A Few Tips For Success
Use room temperature butter for easy creaming. Measure flour by spooning it into the cup and leveling it off. Drain the pineapple well to avoid soggy tops and check the oven a minute early the first time you bake these.
Saving Some For Later
Store cookies in an airtight container at room temperature for up to three days. Freeze baked cookies in a freezer bag for up to two months. Thaw at room temp before serving.
From My Kitchen to Yours
I hope you enjoy this sunny recipe as much as my family does. I like how easy it is to make and how bright the pineapple looks on the cookie. Happy baking from my kitchen to yours.
Your Questions, Answered
How do I keep Pineapple Upside Down Sugar Cookies?
I use room temp butter and a gentle mix to keep the cookies soft in Pineapple Upside Down Sugar Cookies.
Can I make Pineapple Upside Down Sugar Cookies gluten-free?
Yes, you can swap all-purpose flour for a gluten-free blend and still make Pineapple Upside Down Sugar Cookies; textures may vary slightly.
Can I make the dough ahead of time for Pineapple Upside Down Sugar Cookies?
You can make the dough ahead and refrigerate it for a day before baking to give the flavors time to meld in Pineapple Upside Down Sugar Cookies.
Print
Pineapple Upside Down Sugar Cookies That Delight Every Bite
- Total Time: 27 minutes
- Yield: 24 cookies 1x
- Diet: Vegetarian
Description
Bright and simple pineapple upside down sugar cookies that taste like cake with a fruity twist.
Ingredients
- 1 cup unsalted butter (softened)
- 1 cup granulated sugar
- 1 large egg
- 1 teaspoon vanilla extract (optional)
- 2 cups all-purpose flour (or gluten-free blend)
- 1 teaspoon baking soda
- 1/2 teaspoon salt
- 1 can canned pineapple rings (well-drained)
- 2 tablespoons additional sugar for sprinkling
Instructions
- Preheat the oven to 350°F (175°C).
- Cream the butter and 1 cup sugar until light.
- Beat in the egg and vanilla until smooth.
- Whisk the flour, baking soda, and salt in a bowl.
- Stir the dry mix into the wet mix until a soft dough forms.
- Scoop dough into small balls and place on a baking sheet.
- Flatten each ball slightly and set one pineapple ring on top.
- Sprinkle each ring with a little of the 2 tablespoons sugar.
- Bake until edges are set, about 10 to 12 minutes.
- Let cool on the baking sheet for 5 minutes, then move to a rack to cool fully.
Notes
For a softer top, use crushed pineapple or add a maraschino cherry for color. Store cookies in an airtight container at room temperature for up to three days.
- Prep Time: 15 minutes
- Cook Time: 12 minutes
- Category: Dessert
- Method: Baking
- Cuisine: American
Nutrition
- Serving Size: 1 cookie
- Calories: 160
- Sugar: 12g
- Sodium: 150mg
- Fat: 7g
- Saturated Fat: 4g
- Unsaturated Fat: 2g
- Trans Fat: 0g
- Carbohydrates: 22g
- Fiber: 0g
- Protein: 2g
- Cholesterol: 30mg
Keywords: cookies, dessert, pineapple, upside down, baking