Can I use fresh pineapple instead of canned?

Yes! Just slice it thin and pat it dry. Fresh pineapple can be juicier, so drying it well really matters for Pineapple Upside Down Sugar Cookies.

How do I store leftovers?

Store in an airtight container at room temp for 2 days , or in the fridge for up to 5 days . If stacking, place parchment between layers to protect the pineapple tops.

Can I freeze Pineapple Upside Down Sugar Cookies?

You can freeze the baked cookies, but the pineapple texture may soften after thawing. For best results, freeze them in a single layer first, then transfer to a freezer bag for up to 2 months .

Can I make the dough ahead?

Yes—make the dough, cover it, and refrigerate up to 24 hours . Let it sit out for 10–15 minutes so it’s scoopable, then top with pineapple and bake.

What if I only have salted butter?

Use it, but reduce the added salt in the recipe. (Your cookies shouldn’t taste like a beach snack.)

Pineapple Upside Down Sugar Cookies: Joyful, Irresistible 12

Description

Pineapple Upside Down Sugar Cookies are soft, buttery sugar cookies topped with caramelized pineapple rings and sweet cherry centers. This fun twist on the classic cake delivers tropical flavor in an easy, handheld dessert perfect for parties, holidays, or everyday baking.

Ingredients

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For the Cookie Base

1 cup unsalted butter, softened
1 cup granulated sugar
1 large egg
1 teaspoon vanilla extract
2 ½ cups all-purpose flour
1 teaspoon baking soda
½ teaspoon salt

For the Topping

1 can pineapple rings, well drained
Maraschino cherries (optional, for centers)
2–3 tablespoons granulated sugar (for sprinkling)

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Instructions

Preheat oven to 350°F (180°C). Line baking sheets with parchment paper.
In a large bowl, cream softened butter and sugar for 2–3 minutes until light and fluffy.
Add egg and vanilla extract. Beat until fully combined.
In a separate bowl, whisk flour, baking soda, and salt.
Gradually mix dry ingredients into the wet ingredients until a soft dough forms.
Scoop about 2 tablespoons of dough per cookie onto prepared baking sheets, spacing 2 inches apart.
Gently press a well-drained pineapple ring into each dough mound. Add a cherry in the center if using.
Sprinkle additional sugar over the pineapple rings to enhance caramelization.
Bake for 11–13 minutes, until edges are golden and centers are set.
Cool on the baking sheet for 5 minutes, then transfer to a wire rack to cool completely.

Notes

Pat pineapple rings dry to prevent excess moisture.
For extra caramel flavor, replace ¼ cup granulated sugar with brown sugar.
Store in an airtight container at room temperature for up to 2 days or refrigerate up to 5 days.
Dough can be made ahead and refrigerated for up to 24 hours.
Fresh pineapple may be used if sliced thin and dried well.

Prep Time: 15 minutes
Cook Time: 13 minutes
Category: Dessert
Method: Baking
Cuisine: American

Nutrition

Serving Size: 1 cookie
Calories: 210 kcal
Sugar: 15 g
Sodium: 115 mg
Fat: 10 g
Saturated Fat: 6 g
Unsaturated Fat: 3 g
Trans Fat: 0 g
Carbohydrates: 28 g
Fiber: 1 g
Protein: 2 g
Cholesterol: 35 mg