Golden Pineapple Upside Down Sugar Cookies
Golden Pineapple Upside Down Sugar Cookies are the best way to satisfy your sweet tooth. After making these many times, I discovered the trick to a perfect caramelized pineapple topping. Jump to the recipe or keep reading for my best tips. If you love recipes like this, you’ll also enjoy The Ultimate Bakery-Size Orange Scone Cookies and Chicken Broccoli Rice Casserole.
Why This Golden Pineapple Upside Down Sugar Cookies Is Pure Comfort
- Golden, crispy cookies with a warm, gooey pineapple topping.
- Easy to make with simple ingredients.
- Better than takeout and perfect for any occasion.
What You'll Need for Golden Pineapple Upside Down Sugar Cookies
Choosing the right ingredients makes a big difference, but this recipe is forgiving enough to work with what you have.
- 1 can pineapple slices
- 1/2 cup butter
- 3/4 cup brown sugar
- 1 tsp vanilla extract
- 2 cups all-purpose flour
- 1/2 tsp baking soda
- 1/2 tsp salt
- 1/2 cup granulated sugar
- 1 egg
- 1 tsp ground cinnamon
- 1/2 tsp nutmeg
- Optional: Maraschino cherries (optional)
📝 Ingredient Notes
- Pineapple slices: Reserve the juice for the topping.
🛒 Tools & Equipment I Recommend
- High-quality baking sheet — Ensures even baking and golden cookies. → See on Amazon
- Pineapple can opener — Makes opening pineapple cans a breeze. → See on Amazon
How to Make Golden Pineapple Upside Down Sugar Cookies
- Prepare the topping: Melt butter in a saucepan. Stir in brown sugar, reserved pineapple juice, and vanilla. Arrange pineapple slices in a greased 9×13-inch baking dish. Pour the mixture over the pineapple.
- Make the dough: In a separate bowl, combine flour, baking soda, salt, cinnamon, and nutmeg. In another bowl, cream butter and granulated sugar. Beat in the egg, then gradually add the dry ingredients. Chill the dough for 1 hour.
- Bake the cookies: Preheat the oven to 375°F (190°C). Break off pieces of dough and place them on top of the pineapple slices. Bake for 15-20 minutes or until golden brown. Let cool for 5 minutes, then invert onto a serving plate.
Cook's Tips for Perfect Golden Pineapple Upside Down Sugar Cookies
- : For a more even topping, use a cookie scoop to place dough on the pineapple slices.
- Common mistake and fix: If the cookies are too soft, add more flour to the dough. If they're too hard, add a bit more butter.
- : For a fun twist, add maraschino cherries to the center of each cookie before baking.
- : Store any leftovers in an airtight container at room temperature for up to 3 days.
Storing & Reheating Golden Pineapple Upside Down Sugar Cookies
Short-Term Storage
Store in an airtight container in the fridge. Store in an airtight container at room temperature for up to 3 days. Make-ahead tip: Prepare the topping and dough up to 1 day ahead. Assemble and bake just before serving.
Freezing Golden Pineapple Upside Down Sugar Cookies
Not recommended.
How to Reheat Without Drying It Out
Oven: Not necessary. Microwave: Not recommended.
Recipe Notes
- Chef tip: For a more even topping, use a cookie scoop to place dough on the pineapple slices.
- Best substitution: Replace pineapple with peaches or apples for a different flavor.
- Make-ahead: Prepare the topping and dough up to 1 day ahead. Assemble and bake just before serving.
- Scaling: This recipe can be halved or doubled depending on your needs.
- Troubleshooting: If the cookies are too soft, add more flour to the dough. If they're too hard, add a bit more butter.
Want to level up this recipe?
High-quality cooling rack — Allows cookies to cool evenly and prevents sogginess. → Check price on Amazon
Golden Pineapple Upside Down Sugar Cookies
Ingredients
Main Ingredients
- 1 can pineapple slices
- 1/2 cup butter
- 3/4 cup brown sugar
- 1 tsp vanilla extract
- 2 cups all-purpose flour
- 1/2 tsp baking soda
- 1/2 tsp salt
- 1/2 cup granulated sugar
- 1 egg
Seasonings
- 1 tsp ground cinnamon
- 1/2 tsp nutmeg
Optional Toppings
- Maraschino cherries (optional)
Instructions
- Prepare the topping: Melt butter in a saucepan. Stir in brown sugar, reserved pineapple juice, and vanilla. Arrange pineapple slices in a greased 9×13-inch baking dish. Pour the mixture over the pineapple.
- Make the dough: In a separate bowl, combine flour, baking soda, salt, cinnamon, and nutmeg. In another bowl, cream butter and granulated sugar. Beat in the egg, then gradually add the dry ingredients. Chill the dough for 1 hour.
- Bake the cookies: Preheat the oven to 375°F (190°C). Break off pieces of dough and place them on top of the pineapple slices. Bake for 15-20 minutes or until golden brown. Let cool for 5 minutes, then invert onto a serving plate.
Notes
- Chef tip: For a more even topping, use a cookie scoop to place dough on the pineapple slices.
- Best substitution: Replace pineapple with peaches or apples for a different flavor.
- Make-ahead: Prepare the topping and dough up to 1 day ahead. Assemble and bake just before serving.
- Scaling: This recipe can be halved or doubled depending on your needs.
- Troubleshooting: If the cookies are too soft, add more flour to the dough. If they're too hard, add a bit more butter.
Storage
- Fridge: Store in an airtight container at room temperature for up to 3 days.
- Freezer: Not recommended.
- Oven reheat: Not necessary.
- Microwave reheat: Not recommended.
- Make ahead: Prepare the topping and dough up to 1 day ahead. Assemble and bake just before serving.
Nutrition Per Serving
- Calories: 180
- Protein: 2g
- Fat: 8g
- Carbs: 26g
- Fiber: 1g
- Sugar: 15g
- Sodium: 120mg
- Cholesterol: 30mg
- Sat. Fat: 5g
Nutritional values are estimates only. Actual values may vary by brand and portion size.
Golden Pineapple Upside Down Sugar Cookies FAQs
Yes, prepare the topping and dough up to 1 day ahead. Assemble and bake just before serving.
If the cookies are too hard, add a bit more butter to the dough.
No, canned pineapple has a higher sugar content and will caramelize better.
No, the air fryer is not suitable for this recipe.
Store in an airtight container at room temperature for up to 3 days.
A Warm Final Note
I can’t wait for you to try Golden Pineapple Upside Down Sugar Cookies and see how effortlessly it comes together. When you make it, pop back here and leave a rating or share how it turned out — I love hearing from you!
