These Pineapple Upside-Down Sugar Cookies combine the nostalgic charm of a classic pineapple upside-down cake with the soft, buttery goodness of sugar cookies. Each cookie features a caramelized pineapple ring and cherry on top—beautiful, bright, and irresistibly delicious.

Why You’ll Love This Recipe

These cookies are fun to make, visually stunning, and perfect for parties or gifting. They offer a tropical twist on a familiar dessert, with a gooey caramel topping and tender sugar cookie base. The recipe uses simple ingredients, requires no special equipment, and delivers a bakery-quality treat right from your own kitchen.

Ingredients

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

Topping

4 tbsp butter
1/2 cup brown sugar
8–10 pineapple rings, well drained
8–10 maraschino cherries

Sugar Cookie Dough

1/2 cup butter, softened
1 cup granulated sugar
1 egg
2 tsp vanilla extract
1 1/2 cups all-purpose flour
1/2 tsp baking soda
1/4 tsp baking powder
1/4 tsp salt

Directions

1. Prepare the Baking Sheet
   Line a large baking sheet with parchment paper and lightly grease the parchment so the caramel does not stick.
2. Make the Caramel Topping
   Melt the 4 tbsp butter in a small saucepan.
   Stir in the 1/2 cup brown sugar and cook until bubbly and thick, about 1 minute.
   Spoon a 1 1/2–2 teaspoon puddle of caramel onto the parchment for each cookie.
   Place one pineapple ring over each caramel puddle and add a maraschino cherry to the center of each ring.
3. Prepare the Sugar Cookie Dough
   Cream the softened butter and granulated sugar together until fluffy.
   Beat in the egg and vanilla extract.
   Mix in the flour, baking soda, baking powder, and salt until a soft dough forms.
4. Assemble the Cookies
   Scoop 2–3 tablespoons of cookie dough per cookie.
   Flatten each portion slightly with your hands.
   Place each flattened dough disc directly on its pineapple ring, pressing gently so it adheres.
5. Bake
   Bake at 350°F (175°C) for 12–15 minutes, or until the edges are lightly golden.
   Allow the cookies to cool for 8–10 minutes to let the caramel set.
   Carefully flip each cookie over so the pineapple ring becomes the top.

Servings and timing

This recipe makes 8–10 large cookies.
Prep time: approximately 15 minutes
Cook time: 12–15 minutes
Cooling time: about 10 minutes
Total time: around 35–40 minutes

Variations

• Add a pinch of cinnamon to the caramel for a warm, spiced flavor.
• Replace vanilla with a dash of rum extract for a tropical twist.
• Use crushed pineapple instead of rings for a more rustic cookie top.
• Add a handful of shredded coconut to the cookie dough for extra texture.

Storage/Reheating

Store cookies in an airtight container at room temperature for up to 3 days.
For longer storage, refrigerate for up to 5 days.
To freeze, wrap cookies individually and freeze for up to 2 months; thaw at room temperature before serving.
Reheat gently in the oven at 300°F (150°C) for 5 minutes if you want to refresh the texture.

FAQs

How do I keep the cookies from spreading too much?

Ensure the pineapple rings are well drained. If needed, chill the dough for 10 minutes before assembling.

Can I use fresh pineapple instead of canned?

Yes, as long as the slices are cut to similar thickness and well drained.

Can I make the dough ahead of time?

Yes, the dough can be refrigerated for up to 24 hours before baking.

Do I need to flip the cookies while they’re hot?

Allow them to cool for 8–10 minutes first so the caramel sets slightly and flips cleanly.

Can I use light brown sugar instead of dark?

Light brown sugar works perfectly for this recipe.

Why did my caramel leak?

Too much moisture from the pineapple can cause leaking; pat the rings dry before baking.

Can I make smaller cookies?

Yes; use half-size pineapple slices and reduce baking time to 9–11 minutes.

Can I use parchment without greasing?

Lightly greasing is recommended to prevent the caramel from sticking.

Can I add nuts?

Chopped pecans or walnuts can be sprinkled over the caramel before placing the pineapple ring.

How do I know when the cookies are done?

The edges should be lightly golden while the centers remain soft.

Conclusion

These Pineapple Upside-Down Sugar Cookies are the perfect blend of classic flavors and delightful presentation. With their caramelized fruit topping and soft sugar cookie base, they bring a touch of sunshine to any dessert table. Simple to prepare and always a crowd-pleaser, they’re sure to become a favorite in your baking rotation.

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