Looking for a fun and unique twist on a classic dessert? These Pineapple Upside Down Cookies are the perfect combination of chewy, buttery cookie dough and the sweet, caramelized flavors of a traditional pineapple upside-down cake. With a soft cookie base topped with a delightful slice of pineapple, a maraschino cherry, and a touch of brown sugar, these cookies are as visually appealing as they are delicious!

Why You’ll Love This Recipe

Pineapple Upside Down Cookies offer all the sweetness and tropical flavors of the classic cake but in cookie form! The combination of pineapple, brown sugar, and maraschino cherries brings a burst of flavor to every bite. These cookies are fun to make and even more fun to eat. They’re perfect for any occasion, whether you’re serving them at a party, baking them for a special treat, or just enjoying them as a unique snack. Plus, they’re easy to make and require just a few ingredients you likely already have on hand.

Pineapple Upside Down Cookies

Ingredients

1 1/2 cups all-purpose flour
1/2 teaspoon baking soda
1/4 teaspoon salt
1/2 cup unsalted butter, softened
1/2 cup brown sugar, packed
1 large egg
1 teaspoon vanilla extract
1/4 cup sour cream
1/4 cup crushed pineapple, drained (reserve juice)
12 maraschino cherries, halved (or one per cookie)
2 tablespoons brown sugar (for the topping)

(Tip: You’ll find the full list of ingredients and measurements in the recipe card below.)

Directions

Preheat the oven: Preheat your oven to 350°F (175°C). Line a baking sheet with parchment paper or a silicone baking mat.
Prepare the cookie dough: In a medium bowl, whisk together the flour, baking soda, and salt. Set aside. In a separate large bowl, beat the softened butter and brown sugar together until light and fluffy, about 2-3 minutes.
Add the wet ingredients: Add the egg, vanilla extract, and sour cream to the butter mixture and beat until smooth and combined. Stir in the crushed pineapple, making sure it’s well-drained to avoid excess moisture.
Combine the dry and wet ingredients: Gradually add the dry ingredients to the wet mixture, stirring until just combined. The dough should be soft but not too sticky.
Form the cookies: Scoop out about 1 tablespoon of dough and roll it into a ball. Place the dough balls on the prepared baking sheet, spacing them about 2 inches apart.
Prepare the topping: Gently press a pineapple half into the center of each dough ball, then sprinkle a small amount of brown sugar (about 1/2 teaspoon) over each cookie. Add a maraschino cherry half on top of the pineapple.
Bake the cookies: Bake for 10-12 minutes or until the edges are golden brown. The cookies will puff up slightly but should remain soft in the center.
Cool and serve: Let the cookies cool on the baking sheet for 5 minutes, then transfer them to a wire rack to cool completely.

Servings and Timing

Servings: 12 cookies
Preparation time: 15 minutes
Baking time: 10-12 minutes
Total time: 30 minutes

Variations

Add Coconut: For an extra tropical twist, sprinkle shredded coconut on top of the pineapple before baking.
Use Fresh Pineapple: Fresh pineapple can be used in place of canned, but be sure to finely chop and drain it well.
Make Them Gluten-Free: Substitute the all-purpose flour with a gluten-free flour blend to make these cookies gluten-free.
Chocolate Drizzle: For a fun and indulgent twist, drizzle melted chocolate over the cooled cookies for added flavor and visual appeal.
Use Different Fruit: Swap the pineapple with other fruits like peaches or mangoes for a different flavor profile.

Storage/Reheating

Storage: Store the cookies in an airtight container at room temperature for up to 4-5 days. They will stay fresh and soft.
Freezing: You can freeze the cookie dough before baking. Roll the dough into balls and place them on a baking sheet. Freeze for 1-2 hours, then transfer to a freezer bag or container. When ready to bake, place the frozen dough balls on the baking sheet and bake as directed, adding a couple of extra minutes to the baking time.
Reheating: To reheat, place the cookies on a baking sheet and warm them in the oven at 300°F (150°C) for 5 minutes.

FAQs

1. Can I make these cookies with fresh pineapple?

Yes, fresh pineapple can be used, but make sure to finely chop and drain it well to prevent excess moisture from affecting the dough.

2. Can I use pineapple juice in the dough?

You can use a small amount of pineapple juice for added flavor if you like, but make sure not to add too much, as it could make the dough too runny.

3. Can I make these cookies ahead of time?

Yes, you can prepare the dough ahead of time and refrigerate it for up to 2 days before baking. You can also freeze the dough balls to bake later.

4. Can I use margarine instead of butter?

Yes, you can substitute margarine for butter, but the flavor and texture may differ slightly. Butter gives the cookies a richer taste.

5. How can I make the cookies crispier?

If you prefer crispier cookies, you can bake them a little longer, but be careful not to burn them. Check after the 12-minute mark to avoid overbaking.

6. Can I substitute the sour cream with something else?

You can substitute the sour cream with plain yogurt, buttermilk, or even cream cheese for a slightly different texture and taste.

7. Can I use a different fruit topping?

Absolutely! You can use any fruit you like, such as peaches, apricots, or even berries, for a different flavor combination.

8. Can I skip the maraschino cherry topping?

Yes, if you prefer, you can skip the maraschino cherry topping and use just the pineapple for a simpler cookie.

9. How do I prevent the pineapple from getting soggy on top of the cookie?

Make sure to drain the pineapple very well to remove excess moisture before placing it on top of the cookie dough. This helps prevent it from becoming soggy while baking.

10. Can I make these cookies vegan?

To make these cookies vegan, you can substitute the butter with vegan butter, the egg with a flax egg (1 tablespoon ground flaxseed + 3 tablespoons water), and use dairy-free sour cream or yogurt.

Conclusion

Pineapple Upside Down Cookies are a delightful twist on the classic dessert, bringing tropical flavors and a fun presentation to your cookie jar. The combination of soft, chewy cookie dough, caramelized pineapple, and sweet maraschino cherry creates a perfect balance of flavors and textures. These cookies are sure to be a hit at your next gathering or as a sweet treat for yourself. Simple, delicious, and utterly unique, they offer a fun way to enjoy the beloved pineapple upside-down cake in cookie form!