Introduction
Do you love the sweet and fruity taste of pineapple upside-down cake? What if we told you that you could enjoy the same flavor in a fun, bite-sized treat? That’s right—Pineapple Upside-Down Cookies are here to steal the show! These cookies are soft, buttery, and topped with juicy pineapple and a cherry on top.
They’re perfect for parties, picnics, or just a sweet snack at home. The best part? You don’t need to be a baking pro to make them. The recipe is super simple, and even beginners can get it right. So, if you’re craving something tropical, fun, and easy to make, let’s dive right into this delicious cookie recipe!
Ingredients – Pineapple Upside-Down Cookies
To make around 18–20 pineapple upside-down cookies, here’s what you’ll need:
For the Topping:
- ½ cup brown sugar (light or dark)
- ¼ cup unsalted butter (melted)
- 10 pineapple rings (cut in halves or quarters)
- 10 maraschino cherries (cut in half)
For the Cookie Dough:
- 1½ cups all-purpose flour
- ½ teaspoon baking powder
- ¼ teaspoon salt
- ½ cup unsalted butter (softened)
- ¾ cup granulated sugar
- 1 egg
- 1 teaspoon vanilla extract
Step-by-Step Process – Pineapple Upside-Down Cookies
Step 1: Preheat the Oven
Start by preheating your oven to 350°F (175°C). This will make sure your cookies bake evenly.
Step 2: Prepare Your Muffin Pan
Take a regular-size muffin tin and lightly grease each cup with non-stick spray or a little butter. This helps the cookies come out easily after baking.
Step 3: Add the Topping
In a small bowl, mix the brown sugar and melted butter together. Then, spoon about 1 teaspoon of the mixture into the bottom of each muffin cup.
Next, place a small piece of pineapple (half or quarter of a ring) on top of the sugar-butter mix. Add half a maraschino cherry in the center of the pineapple. This makes the cookies look just like mini upside-down cakes!
Step 4: Make the Cookie Dough
In a medium bowl, whisk together the flour, baking powder, and salt.
In another larger bowl, use a hand mixer or whisk to beat the softened butter and granulated sugar until the mix is light and fluffy. Then add the egg and vanilla extract, and mix again until smooth.
Now slowly add the dry flour mixture into the wet butter mixture. Mix until everything is combined and forms a soft dough.
Step 5: Shape and Fill
Take a tablespoon of cookie dough and gently flatten it into a small disc shape. Place it on top of the pineapple and cherry in the muffin tin. Try to cover the fruit completely. Repeat until all cups are filled.
Step 6: Bake
Put the muffin tray into your preheated oven and bake for 15 to 18 minutes, or until the cookie tops are light golden brown.
Step 7: Cool and Flip
Once baked, remove the tray from the oven and let it cool for 5 minutes.
After that, take a butter knife and carefully loosen the edges of each cookie. Then, place a tray or baking sheet over the muffin pan and flip the whole thing upside down to release the cookies.
Let the cookies cool for a few more minutes before serving.
Nutritional Information
| Nutrient | Amount |
|---|---|
| Calories | 140–160 |
| Total Fat | 7g |
| Saturated Fat | 4g |
| Carbohydrates | 20g |
| Sugar | 12g |
| Protein | 1g |
| Fiber | 0.5g |
| Sodium | 70mg |
| Cholesterol | 20mg |
Frequently Asked Questions
Q1. Can I use canned pineapple for this recipe?
Yes! Canned pineapple rings work great. Just be sure to drain them well before using so the cookies don’t turn soggy.
Q2. What if I don’t have a muffin pan?
You can try using mini cake molds or a silicone baking mold. Just make sure each section is deep enough to hold the fruit and dough.
Q3. Can I use boxed cookie dough?
You can, but homemade dough gives the best flavor. If you’re short on time, sugar cookie dough from the store can be a quick substitute.
Q4. How should I store the cookies?
Keep your cookies in an airtight container at room temperature for up to 3 days. You can also refrigerate them for up to 5 days.
Q5. Can I freeze Pineapple Upside-Down Cookies?
Yes! Let them cool completely, then wrap each cookie in plastic wrap and store in a freezer-safe bag for up to 2 months. When you want to eat one, thaw it at room temperature or microwave it for 10–15 seconds.
Q6. Can I make them gluten-free?
Yes, you can use a 1:1 gluten-free flour blend instead of regular flour. The texture might be a little different, but they’ll still taste great.
Final Thoughts
And there you have it—Pineapple Upside-Down Cookies that are easy to make, fun to eat, and full of tropical flavor! Whether you’re baking them for a party, a family treat, or just because you’re craving something sweet, these cookies are sure to be a hit.
The combination of buttery cookie dough with caramelized pineapple and cherry creates a flavor that’s both familiar and exciting. Plus, making them in a muffin tin gives each cookie a perfect shape and portion.
Even if you’re new to baking, don’t worry. Just follow each step, and you’ll be surprised by how simple it is. So, grab your apron, preheat the oven, and let the sweet aroma of pineapple cookies fill your kitchen. Happy Baking!


