Pineapple Upside Sugar Cookies

If you adore the buttery charm of sugar cookies and crave the sweet-tart zing of pineapple, these Pineapple Upside Sugar Cookies are calling your name. A soft, chewy sugar cookie meets caramelized pineapple in every bite—bringing a tropical twist to classic comfort. Whether you’re baking for a gathering or just a cozy night in, these treats are guaranteed to impress.


💛 What Makes Them Special

  • Tropical Brightness: Juicy pineapple delivers a burst of island flavor.
  • Perfect Texture: Soft, tender sugar cookies with a golden edge.
  • Quick Bake: Done in under 30 minutes—perfect for last-minute cravings.
  • Fun to Customize: Add-ins like coconut, nuts, or a sweet glaze make them uniquely yours.

🛒 Ingredients (Yields 12–16 Cookies)

PartIngredientAmountNotes
ToppingPineapple (fresh or canned)1, thinly slicedCanned rings work if short on time
Melted unsalted butter2 tablespoons
Brown sugar2 tablespoons
Ground cinnamon (optional)¼ teaspoonAdds warm spice
Cookie DoughSoftened unsalted butter1 cup
Granulated sugar1 cup
Large egg1
Pure vanilla extract1 teaspoon
All-purpose flour2¼ cups
Baking powder1 teaspoon
Salt¼ teaspoon

👩‍🍳 Step-by-Step Instructions

1. Preheat Oven
Set to 350°F (175°C). Line a baking sheet with parchment or lightly grease it.

2. Prepare the Pineapple Topping

  • Brush each pineapple slice with melted butter.
  • Sprinkle with brown sugar and cinnamon (if using).
  • Lay flat on the prepared baking sheet.

3. Make the Sugar Cookie Dough

  • Cream butter and sugar together until fluffy.
  • Add the egg and vanilla; mix until smooth.
  • In another bowl, whisk flour, baking powder, and salt.
  • Slowly add dry ingredients to the wet mixture and mix until combined.

4. Assemble Cookies

  • Scoop 1–2 tablespoons of dough and flatten into a round.
  • Gently place each dough disc on top of a pineapple slice, pressing lightly to cover.

5. Bake

  • Bake for 12–15 minutes until edges are just golden.
  • Let cool for 2–3 minutes on the baking sheet.

6. Flip & Finish

  • Carefully flip each cookie so the pineapple is on top.
  • Optional: Drizzle with a powdered sugar glaze or sprinkle with coconut for extra flair.

🌟 Baking Tips

  • Fresh is Best: Use fresh pineapple for more natural caramelization.
  • Add Some Crunch: Chopped pecans or macadamia nuts pair beautifully.
  • Flavor Boost: Swap brown sugar with coconut sugar for deeper sweetness.
  • Storage: Store in an airtight container at room temp for 2 days or refrigerate for up to 5. Let return to room temperature before serving.

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