Pineapple Upside Sugar Cookies – Easy Tropical Treat

Imagine taking the buttery sweetness of a classic sugar cookie and swapping in the juicy charm of a golden pineapple ring—yes, you’re reading the right thing. These Pineapple Upside Sugar Cookies deliver that nostalgic coziness of a sugar‑cookie bake with the tropical flair of a pineapple‑upside‑down‑cake vibe. If you grew up loving your grandma’s pineapple desserts or you crave a breezy island twist to your cookie tray, this is your ticket. I’ve got a soft spot for them because as a kid I begged my mom to turn pineapple ring desserts into cookies—and now here we are, delivering pineapple dessert ideas in cookie form.

Why You’ll Love These Pineapple Sugar Cookies

• Showstopping looks – A pineapple ring (or bite‑sized version) perched atop each cookie gives you fruit‑topped cookie charm and pineapple‑ring desserts flair.
  
• Easy for beginners – No overly fussy technique, just cookie dough with a twist of tropical baking.
  
• Tropical‑meets‑cozy flavor – Think “pineapple baked goods” meets “pineapple sugar cookies” with that familiar sugar‑cookie base.
  
• Great for parties – These fruity cookies make fantastic pineapple party dessert bites or summer fruit desserts on the go.
  

History of Pineapple Treats & Sugar Cookies

The Origins of Pineapple Upside‑Down Cake Cookies

• The concept of an upside‑down cake—fruit or topping placed at the bottom of the pan, batter poured on top, baked and then flipped—can be traced to Europe in the Middle Ages.
  
• In America, an early version of an “upside‑down” cake using prunes surfaced around 1923.
  
• The iconic pineapple version owes its popularity to the canned pineapple boom and campaigns around the 1920s–30s. For example, the Dole company ran a pineapple recipe contest in 1925 which boosted the pineapple upside‑down cake’s fame.
  

Where Sugar Cookies Came From

• The modern sugar cookie (buttery, vanilla‑tinged, with flour, sugar, eggs, baking powder) traces back to German‑Protestant settlers in Nazareth, Pennsylvania in the 1700s.
  
• Earlier cookie‑style sweets date even further back: cookie‑like cakes go to 7th‑century Persia.
  

Ingredients for Pineapple-Flavored Cookies

Here’s what you’ll need for about 24 cookies:

• 2 ½ cups (312 g) all‑purpose flour
  
• 1 tsp baking powder
  
• ½ tsp salt
  
• 1 cup (226 g) unsalted butter, room temperature
  
• 1 cup (200 g) granulated sugar (plus optional extra for topping)
  
• 1 large egg, room temperature
  
• 1 tsp pure vanilla extract
  
• ¼ cup (60 ml) canned pineapple juice (from the canned pineapple rings)
  
• 12 canned pineapple rings, drained and patted dry (or 24 pineapple ring halves)
  
• Optional: extra coarse sugar (turbinado) for sprinkling on top
  

How to Make Pineapple Upside-Down Cake Cookies

1. Make the dough base: In one bowl, whisk flour, baking powder, and salt. In another, cream butter and sugar until fluffy. Add egg, vanilla, and pineapple juice. Mix dry into wet until just combined.
   
2. Portion the dough: Use a 2 Tbsp cookie scoop to form dough balls and place them on a parchment-lined baking sheet.
   
3. Add the pineapple: Press a drained pineapple ring or half ring gently into each dough ball. Optional: sprinkle coarse sugar on top.
   
4. Bake: Preheat oven to 350°F (175°C). Bake cookies for 12–14 minutes, until edges are golden.
   
5. Cool: Let cookies rest on the baking sheet for 5 minutes, then transfer to a wire rack to cool completely.
   

Baking Tips & Tropical Cookie Variations

Smart Baking Tips for Pineapple Cookies

• Drain pineapple well — Excess juice will cause cookies to spread too much or get soggy.
  
• Use parchment or silicone — Makes removal and cleanup easier, and helps browning evenly.
  
• Chill dough if needed — If the dough is very soft, pop in fridge for 15 minutes so cookies hold shape.
  
• Cookie scoop — Ensures uniform size so you get consistent bake time.
  
• Let them rest — After baking, allow a few minutes on the sheet so the pineapple‑topped cookie sets, then finish cooling on wire rack.
  

Creative Spins on Pineapple Cookie Ideas

• Peach swap — Use drained canned peach rings instead of pineapple for a peachy version of pineapple proud (still counts as tropical baking!).
  
• Maraschino cherry peak — Press a maraschino cherry into the center of each pineapple ring for a retro pineapple‑upside‑down‑cake cookie look.
  
• Add spice — Stir in ¼ tsp ground ginger or cinnamon to the dough to enrich the flavor profile.
  

How to Store, Reheat, and Prep Pineapple Baked Goods

• Storage: Store cooled cookies in an airtight container at room temperature for up to 3 days.
  
• Reheating: Microwave a cookie for 8–10 seconds to revive that soft texture (pineapple‑topped bit will warm nicely).
  
• Make‑ahead dough: Prepare dough up to step 6, cover and refrigerate for up to 2 days. Bring to room temperature, then portion and bake as directed.
  

Serving Pineapple Party Desserts with Style

• Pair with an iced chai or a pineapple iced tea to lean into the tropical cookie recipe vibes.
  
• Perfect for a brunch dessert platter, or as part of a tropical‑themed gathering—these cookies are pineapple party dessert ready.
  
• Serve alongside other pineapple baked goods and fruity cookies — they’ll complement each other in a fruit‑topped cookies spread.
  

FAQ About Making Fruity Cookies with Pineapple

More and Related Pineapple Upside Sugar Cookies Recipes

• Grandma’s Pineapple Dream Dessert
  
• Coconut Pineapple Bites
  
• Strawberry Banana Pudding
  
• Soft Batch Chocolate Chip Cookies
  
• Best Soft Batch Chocolate Chip Cookie
  
• Cotton Candy Cookies
  

Conclusion + Call to Action

There you have it—your easy, fun, and flavour‑packed recipe for Pineapple Upside Sugar Cookies, a tropical cookie recipe that’s also steeped in comfort and nostalgia. If you’re ready to bring pineapple dessert ideas, pineapple‑upside‑down‑cake cookies, and pineapple cookie ideas into one delicious batch of fruity cookies, this is your moment. Whip up a tray, share with friends, and watch them disappear. Don’t forget to follow my Pinterest page for even more pineapple treats, tropical baking ideas, pineapple baked goods inspiration and summer fruit desserts: https://www.pinterest.com/emiliorecipes/.
This is the cookie I want to eat—now it’s yours.

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