There’s nothing quite like a buttery, chewy sugar cookie fresh from the oven. But what if we took things up a notch? These Pineapple Upside Sugar Cookies blend the classic cookie experience with the tropical, caramelized delight of a pineapple upside-down cake. They’re golden, chewy, and have a surprise juicy topping of sweet pineapple — a dessert that’s both nostalgic and refreshingly unique.
Perfect for parties, summer get-togethers, or a sweet treat after dinner, these cookies will quickly become a favorite in your baking rotation. With simple pantry ingredients and canned pineapple rings, this recipe is as easy as it is delicious.
Why You’ll Love These Cookies
- Tropical Flavor: The pineapple topping adds a juicy, fruity note.
- Soft & Chewy Texture: Thanks to the butter and perfect bake time.
- Visually Appealing: Each cookie is crowned with a beautiful golden pineapple ring.
- Simple Ingredients: Mostly pantry staples with minimal effort.
- Great for Gifting or Entertaining: Unique presentation and flavor profile.
Ingredients (US Cup Measurements)
For the Cookie Dough:
- 1 cup unsalted butter, softened
- 1 cup granulated sugar
- 1 large egg
- 1 tsp vanilla extract
- 2½ cups all-purpose flour
- ½ tsp baking soda
- ¼ tsp salt
For the Topping:
- 10–12 canned pineapple rings, well-drained and patted dry
- Additional sugar for sprinkling
Step-by-Step Instructions
Step 1: Prep the Pineapple
Before starting the dough, place the drained pineapple rings on a paper towel-lined plate. Pat dry thoroughly to avoid extra moisture, which can interfere with cookie texture. Set aside.
Step 2: Make the Cookie Dough
In a large mixing bowl, cream together the softened butter and granulated sugar until light and fluffy, about 2–3 minutes.
Add the egg and vanilla extract, mixing until fully incorporated.
In a separate bowl, whisk together the flour, baking soda, and salt. Gradually add the dry ingredients to the wet mixture, mixing until just combined.
Chill the dough in the refrigerator for at least 30 minutes to make it easier to handle and to help cookies maintain their shape while baking.
Step 3: Preheat the Oven
Preheat your oven to 350°F (175°C). Line two baking sheets with parchment paper or silicone baking mats.
Step 4: Assemble the Cookies
Using a cookie scoop or spoon, scoop about 2 tablespoons of dough and roll it into a ball. Flatten the dough slightly and place it on the baking sheet.
Gently press one pineapple ring onto each cookie dough round. If the ring is too large, you can cut it into halves or quarters and place them in decorative patterns.
Sprinkle the tops with a little extra granulated sugar to promote caramelization.
Step 5: Bake
Bake in the preheated oven for 12–14 minutes, or until the edges are golden and the center is just set. The pineapple should be slightly caramelized.
Allow cookies to cool on the baking sheet for 5 minutes before transferring to a wire rack to cool completely.
Nutrition Information (Per Cookie, Approx. Based on 12 Cookies)
- Calories: ~220 kcal
- Fat: 11g
- Carbohydrates: 29g
- Sugar: 15g
- Protein: 2g
- Fiber: 0.5g
Tips for Perfect Pineapple Upside Sugar Cookies
- Dry the Pineapple Well: This prevents soggy cookies and allows the sugar to caramelize.
- Don’t Overmix: Mix the dough until just combined to avoid tough cookies.
- Chill the Dough: Helps cookies keep their shape while baking.
- Use Quality Butter: It’s a key flavor in this recipe, so go for real unsalted butter.
- Smaller Pineapple Pieces: For a cleaner look or better fit, trim pineapple rings as needed.
Variations and Additions
- Cherry Center: Place a maraschino cherry in the center of each pineapple ring for a truly retro presentation.
- Brown Sugar Sprinkle: Add a little brown sugar on top instead of granulated sugar for a deeper caramel flavor.
- Coconut Infusion: Mix in a bit of shredded coconut into the dough for a piña colada-style treat.
- Glazed Version: Drizzle with a light vanilla glaze after cooling for extra sweetness.
Make-Ahead & Storage
- Make Ahead: Dough can be made and chilled up to 48 hours in advance.
- Storage: Store baked cookies in an airtight container at room temperature for up to 3 days.
- Freezing: Freeze baked cookies for up to 2 months. Thaw at room temperature before serving.
Serving Suggestions
- Afternoon Tea: A unique and fruity addition to a tea spread.
- Summer Parties: Bright and tropical for warm weather gatherings.
- Dessert Platters: Stand out on cookie trays.
- Gifting: Beautiful and festive in treat boxes or jars.
Final Thoughts
These Pineapple Upside Sugar Cookies offer everything you love about a soft, chewy cookie with a surprise tropical twist. By combining the warm nostalgia of pineapple upside-down cake with the simplicity of sugar cookies, you get a hybrid dessert that’s both comforting and fun.
They’re easy to make, customizable, and guaranteed to draw attention at any gathering. Whether you serve them at a summer cookout or include them in your holiday baking, they’re a sweet surprise that everyone will remember.