What happens when you mix soft sugar cookies with the fruity flair of pineapple rings? You get Pineapple Upside Sugar Cookies, a cheerful bake that brings retro charm to your cookie jar. These golden, buttery treats feature full pineapple rings nestled on top of pillowy sugar cookie dough—like mini upside-down cakes you can hold. They’re eye-catching, beginner-friendly, and just plain fun. If you’re craving something tropical with a nostalgic twist, these cookies are your golden ticket.
Why You’ll Love These Cookies
There’s something magical about Pineapple Upside Sugar Cookies, and here’s why you’ll keep coming back for more:
- Showstopping looks: The pineapple rings add a sunny, vintage vibe.
- Easy for beginners: Simple steps, no fancy gadgets, and foolproof results.
- Tropical-meets-cozy: Fruity pineapple meets buttery sugar cookie perfection.
- Party-ready: Great for bake sales, brunches, or brightening any dessert table.
This is the kind of cookie recipe you’ll love sharing (and showing off).
History or Fun Facts About Pineapple Upside Sugar Cookies
Let’s dig into the tasty roots of this fruity favorite:
- Pineapple upside-down cake first became popular in the 1920s thanks to canned pineapple.
- The upside-down dessert method dates back to the Middle Ages, often with apples or cherries.
- Sugar cookies originated in Pennsylvania Dutch country in the 1700s.
- Combining these two classics in cookie form creates a fun, portable spin on tradition.
Ingredients
- 1 cup unsalted butter, softened
- 1 cup granulated sugar
- 1 egg
- 1 tsp vanilla extract
- 2½ cups all-purpose flour
- ½ tsp baking soda
- ¼ tsp salt
- 10–12 canned pineapple rings, well-drained and patted dry
- Additional sugar for sprinkling
How to Make Pineapple Upside Sugar Cookies
Easy steps for irresistibly fruity cookies:
- Preheat oven to 350°F (175°C) and line baking sheets with parchment paper.
- Cream butter and sugar in a large bowl until light and fluffy.
- Add egg and vanilla, beating until well combined.
- Mix dry ingredients (flour, baking soda, salt) in a separate bowl. Gradually add to the wet mixture until a soft dough forms.
- Roll dough into balls (about 1½ tbsp each), flatten slightly, and place on the baking sheets.
- Top each cookie with a pineapple ring, gently pressing it down.
- Sprinkle sugar on top of each pineapple ring for sparkle and light caramelization.
- Bake for 12–14 minutes, until the edges are golden and centers are set.
- Cool for 5 minutes on the pan, then transfer to a wire rack to cool completely.
Helpful Tips and Creative Spins:
Baking Tips:
- Dry pineapple well to prevent soggy cookies.
- Use parchment paper to avoid sticking and ensure clean bottoms.
- Chill dough if it’s too soft to roll.
- Use a cookie scoop for even sizes.
- Let cookies rest before removing to avoid breaking the pineapple.
Variations:
- Swap pineapple for peach rings for a new fruity vibe.
- Add a maraschino cherry in the center before baking.
- Stir in a pinch of ginger or cinnamon for warm spice notes.
Storage, Reheating, and Make-Ahead Tips for Pineapple Upside Sugar Cookies
- Storage: Store in an airtight container at room temp for up to 3 days.
- Reheating: Microwave for 8–10 seconds to revive their softness and aroma.
- Make-Ahead: Make the dough ahead and refrigerate up to 2 days. Assemble and bake when ready.
Serving Suggestions for Pineapple Upside Sugar Cookies
These cookies love company. Pair them with iced chai or pineapple iced tea for a refreshing snack. Serve alongside grilled kabobs or a brunch charcuterie board for a tropical spread. Want a dessert platter? Include them with coconut macaroons or lemon bars for bright, balanced flavors.
Frequently Asked Questions
Can I use fresh pineapple instead of canned?
Yes! Just cut into thin rings and blot dry to remove excess moisture.
Can I freeze them?
Absolutely—freeze in layers with parchment paper. Thaw at room temp before serving.
What if I don’t have parchment paper?
Grease your baking sheets well or use silicone mats for best results.
Can I reduce the sugar?
You can cut back by 2–3 tablespoons without much difference in texture.
Can I use gluten-free flour?
Yes, just be sure to use a 1:1 baking blend for similar texture.
Enjoy Your Pineapple Upside Sugar Cookies
These Pineapple Upside Sugar Cookies deliver everything you love in one sunny, sweet bite. From the buttery base to the caramelized pineapple top, they blend vintage comfort with fresh tropical flair. Perfect for beginners, party-goers, and pineapple lovers alike—so grab your whisk and give them a try. You might just have a new go-to cookie!
Pineapple Upside Sugar Cookies
Ingredients
- 1 cup unsalted butter, softened
- 1 cup granulated sugar
- 1 egg
- 1 tsp vanilla extract
- 2½ cups all-purpose flour
- ½ tsp baking soda
- ¼ tsp salt
- 10–12 canned pineapple rings, well-drained and patted dry
- Additional sugar for sprinkling
Instructions
- Preheat oven to 350°F (175°C). Line baking sheets with parchment paper.
- In a large bowl, cream butter and sugar until light and fluffy.
- Beat in the egg and vanilla until well combined.
- In a separate bowl, whisk together flour, baking soda, and salt. Gradually add to the butter mixture to form a soft dough.
- Roll dough into 1½ tbsp balls, flatten slightly, and place on baking sheet.
- Top each dough disk with a pineapple ring, pressing gently.
- Sprinkle sugar on top of pineapple for extra sparkle.
- Bake 12–14 minutes until edges are golden. Cool 5 mins, then transfer to a rack.
Notes
Explore More Recipes
Love tropical flavors? Try these next:
- Hawaiian Carrot Pineapple Cake – A moist, fruity delight.
- Coconut Macaroons – Chewy, coconutty bliss.
- Key Lime Pie – Zesty and creamy perfection.
Happy baking!