If you love fruity desserts, this Pineapple Upside Down Sugar Cookies Recipe is perfect for you. These cookies are soft, buttery and full of sweet pineapple flavor. They look beautiful and taste amazing.
This Pineapple Upside Down Sugar Cookies Recipe combines classic sugar cookies with tropical sweetness. You will learn How to make Pineapple Upside Down Sugar Cookies easily at home. The Ingredients for Pineapple Upside Down Sugar Cookies are simple and easy to find.These cookies are great for parties, holidays and family treats. They are colorful and fun to serve.
The Secret Behind This Delicious
The secret is using pineapple rings and brown sugar topping. The brown sugar melts and creates a caramel layer. This makes the cookies shiny and sweet.
Another secret is soft sugar cookie dough. It must stay soft and tender. Do not overbake the cookies.
A small piece of cherry in the center adds color and sweetness. It also gives the classic upside-down cake look.

Recipe Card
- Recipe Name: Pineapple Upside Down Sugar Cookies
- Servings: 18 cookies
- Prep Time: 20 mins
- Cook Time: 15 mins
- Total Time: 35 mins
- Course: Dessert
- Cuisine: American
- Calories: 210 kcal per cookie
Equipment List
- Muffin tin
- Mixing bowls
- Electric mixer
- Measuring cups
- Measuring spoons
- Spatula
- Cooling rack
- Can opener
Ingredients You Need for Pineapple Upside Down Sugar Cookies
- 1 can pineapple rings, drained
- 10 maraschino cherries, halved
- ½ cup unsalted butter, melted
- ¾ cup brown sugar
- 1 cup unsalted butter, softened
- 1 cup granulated sugar
- 1 egg
- 1 teaspoon vanilla extract
- 2 cups all-purpose flour
- 1 teaspoon baking powder
- ½ teaspoon salt
These are the main Ingredients for Pineapple Upside Down Sugar Cookies.
Instructions
- Prepare the Pan
Preheat oven to 350°F. Grease muffin tin lightly to prevent sticking. - Add Butter and Sugar
Pour a small spoon of melted butter into each muffin cup. Sprinkle brown sugar evenly on top. - Add Pineapple
Place one pineapple ring inside each muffin cup. Press gently into brown sugar mixture. - Add Cherry
Place half cherry in center of each pineapple ring. This gives classic upside-down look. - Make Cookie Dough
In a bowl, cream softened butter and sugar until light and fluffy. - Add Wet Ingredients
Mix in egg and vanilla extract. Beat until smooth and well combined. - Add Dry Ingredients
In another bowl, mix flour, baking powder and salt. Slowly add to wet mixture. - Fill the Muffin Cups
Scoop cookie dough over each pineapple ring. Spread gently to cover evenly. - Bake the Cookies
Bake for 12–15 minutes until edges are golden and center is set. - Cool and Flip
Let cookies cool for 5 minutes. Carefully flip onto tray while still warm.
Now you know How to make Pineapple Upside Down Sugar Cookies step by step.
Expert Tips & Variations
- Drain pineapple very well to avoid soggy cookies.
- Pat pineapple dry with paper towel.
- Do not overfill muffin cups with dough.
- Add coconut flakes for tropical flavor.
- Use crushed pineapple for smaller cookie version.
- Chill dough for 20 minutes if too soft.
- Serve warm for best texture.
These tips help perfect your Pineapple Upside Down Sugar Cookies Recipe.
Nutrition Information
| Nutrient | Amount per Cookie |
|---|---|
| Calories | 210 kcal |
| Carbohydrates | 28 g |
| Protein | 2 g |
| Fat | 10 g |
| Sugar | 18 g |
| Sodium | 120 mg |
Values may vary based on ingredients used.
Serving Suggestions
- Serve these cookies slightly warm. The caramel topping tastes best fresh.
- Pair them with vanilla ice cream for extra sweetness. They also taste great with coffee or tea.
- You can dust lightly with powdered sugar for decoration. These cookies are perfect for parties.
Storage & Reheating Tips
- Store cookies in an airtight container at room temperature. They stay fresh for 3 days.
- Refrigerate if weather is warm. Bring to room temperature before serving.
- You can reheat in microwave for 10 seconds. This softens the caramel topping again.
- Freezing is possible. Wrap tightly and store up to 2 months.

Pineapple Upside Down Sugar Cookies Recipe
Ingredients
- 1 can pineapple rings drained
- 10 maraschino cherries halved
- ½ cup unsalted butter melted
- ¾ cup brown sugar
- 1 cup unsalted butter softened
- 1 cup granulated sugar
- 1 egg
- 1 teaspoon vanilla extract
- 2 cups all-purpose flour
- 1 teaspoon baking powder
- ½ teaspoon salt
These are the main Ingredients for Pineapple Upside Down Sugar Cookies.
Instructions
Prepare the Pan
- Preheat oven to 350°F. Grease muffin tin lightly to prevent sticking.
Add Butter and Sugar
- Pour a small spoon of melted butter into each muffin cup. Sprinkle brown sugar evenly on top.
Add Pineapple
- Place one pineapple ring inside each muffin cup. Press gently into brown sugar mixture.
Add Cherry
- Place half cherry in center of each pineapple ring. This gives classic upside-down look.
Make Cookie Dough
- In a bowl, cream softened butter and sugar until light and fluffy.
Add Wet Ingredients
- Mix in egg and vanilla extract. Beat until smooth and well combined.
Add Dry Ingredients
- In another bowl, mix flour, baking powder and salt. Slowly add to wet mixture.
Fill the Muffin Cups
- Scoop cookie dough over each pineapple ring. Spread gently to cover evenly.
Bake the Cookies
- Bake for 12–15 minutes until edges are golden and center is set.
Cool and Flip
- Let cookies cool for 5 minutes. Carefully flip onto tray while still warm.
Now you know How to make Pineapple Upside Down Sugar Cookies step by step.
Notes
- Drain pineapple very well to avoid soggy cookies.
- Pat pineapple dry with paper towel.
- Do not overfill muffin cups with dough.
- Add coconut flakes for tropical flavor.
- Use crushed pineapple for smaller cookie version.
- Chill dough for 20 minutes if too soft.
- Serve warm for best texture.
FAQs about Pineapple Upside Down Sugar Cookies
1. Can I use fresh pineapple instead of canned?
Yes, you can use fresh pineapple slices. Make sure they are thin and well drained before baking.
2. Why are my cookies sticking to the pan?
You may not have greased the pan enough. Always flip cookies while still warm for easier release.
3. Can I make the dough ahead of time?
Yes, you can refrigerate the dough for up to 24 hours. Let it soften slightly before baking.
4. How do I prevent soggy cookies?
Dry the pineapple well with paper towels. Too much juice can make the bottom soft.
5. Can I make these without cherries?
Yes, you can skip cherries if preferred. The cookies will still taste sweet and delicious.
Conclusion
This Pineapple Upside Down Sugar Cookies Recipe is sweet, soft and full of tropical flavor. It is easy and fun to make.
Now you understand How to make Pineapple Upside Down Sugar Cookies step by step. The Ingredients for Pineapple Upside Down Sugar Cookies are simple and affordable.
Try this recipe today. These cookies are colorful, tasty and perfect for sharing. Your family will love every bite.

Sofia Lane is a food lover who loves cooking and sharing easy, tasty recipes. She believes in making cooking simple and fun for everyone. On DiveCrave, Sofia shares her favorite meals, desserts and treats that anyone can make at home.













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