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)
Part | Ingredient | Amount | Notes |
---|---|---|---|
Topping | Pineapple (fresh or canned) | 1, thinly sliced | Canned rings work if short on time |
Melted unsalted butter | 2 tablespoons | ||
Brown sugar | 2 tablespoons | ||
Ground cinnamon (optional) | ¼ teaspoon | Adds warm spice | |
Cookie Dough | Softened unsalted butter | 1 cup | |
Granulated sugar | 1 cup | ||
Large egg | 1 | ||
Pure vanilla extract | 1 teaspoon | ||
All-purpose flour | 2¼ cups | ||
Baking powder | 1 teaspoon | ||
Salt | ¼ 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.