why make this recipe
Pineapple Upside-Down Cookies offer a delightful twist on a classic dessert. They combine the familiar flavors of pineapple upside-down cake with the fun and portability of cookies. These treats are simple to make, and they bring a tropical sweetness to your dessert table. Whether for a special occasion or just to satisfy your sweet tooth, these cookies will impress your family and friends.
how to make Pineapple Upside-Down Cookies
Ingredients:
- Unsalted Butter (½ cup, softened) – Gives the cookies their rich, buttery texture. If using salted butter, reduce the added salt.
- Granulated Sugar (¾ cup) – Provides sweetness and helps with the cookie’s soft structure. Brown sugar can be used for a deeper caramel-like flavor.
- Large Egg (1) – Binds the ingredients together and adds moisture. If allergic to eggs, substitute with a flax egg (1 tbsp ground flaxseed + 3 tbsp water).
- Vanilla Extract (1 tsp) – Enhances the sweetness with warm, aromatic notes.
- All-Purpose Flour (1 ¼ cups) – Forms the cookie’s structure. If needed, use a 1:1 gluten-free flour blend.
- Baking Powder (½ tsp) – Helps the cookies rise slightly and stay soft.
- Salt (¼ tsp) – Balances sweetness and enhances flavors.
- Brown Sugar (½ cup) – Caramelizes during baking, creating the signature upside-down effect.
- Melted Butter (2 tbsp) – Helps the brown sugar create a rich, syrupy base.
- Pineapple Rings (1 small can, cut into smaller pieces) – Provides the tropical fruitiness. Fresh pineapple works too but should be cut into small tidbits for even baking.
- Maraschino Cherries (halved) – Adds a pop of color and sweetness. Fresh cherries or dried cranberries can be used as alternatives.
Directions:
- Prepare the Cookie Dough: In a bowl, mix softened butter, granulated sugar, and brown sugar until creamy. Add the egg and vanilla extract, mixing until well combined. Stir in the flour, baking powder, and salt until you have a soft dough.
- Prepare the Topping: In another bowl, combine melted butter and brown sugar. Mix well, then spread this mixture on the bottom of your cookie pan.
- Assemble the Cookies: Place small spoonfuls of cookie dough on top of the brown sugar mixture. Add pineapple pieces and halved cherries on top of each cookie dough mound.
- Bake the Cookies: Preheat your oven to 350°F (175°C). Bake for 12-15 minutes or until the edges are golden.
- Serve and Enjoy: Let the cookies cool slightly before flipping them on a plate to reveal the delicious toppings.
how to serve Pineapple Upside-Down Cookies
Enjoy these cookies warm or at room temperature. They can be served on their own or with a scoop of vanilla ice cream on the side for an extra treat. They are perfect for parties, gatherings, or just as a sweet snack at home.
how to store Pineapple Upside-Down Cookies
Store the cookies in an airtight container at room temperature for up to five days. If you want them to last longer, you can freeze the cookies. Just place them in a single layer in a freezer-safe container and separate layers with parchment paper. They can be stored frozen for up to three months.
tips to make Pineapple Upside-Down Cookies
- Make sure your butter is softened to room temperature for easy mixing.
- For uniform cookies, use a cookie scoop.
- Adjust the size of the pineapple pieces to ensure even baking.
- Experiment with adding shredded coconut for extra texture and flavor.
variation
You can substitute the pineapple with other fruits like peaches or cherries for a different flavor. Adding nuts like walnuts or pecans can also give a nice crunch.
FAQs
1. Can I use fresh pineapple instead of canned?
Yes, you can use fresh pineapple! Just make sure to cut it into small tidbits for even baking.
2. Can I make these cookies gluten-free?
Absolutely! Use a 1:1 gluten-free flour blend to replace the all-purpose flour.
3. How do I know when the cookies are done?
The cookies are done when the edges are golden brown. Keep an eye on them, as they can bake quickly!

Pineapple Upside-Down Cookies
Ingredients
Cookie Base Ingredients
- ½ cup Unsalted Butter, softened If using salted butter, reduce the added salt.
- ¾ cup Granulated Sugar You can use brown sugar for a deeper caramel-like flavor.
- 1 Large Egg If allergic to eggs, substitute with a flax egg (1 tbsp ground flaxseed + 3 tbsp water).
- 1 tsp Vanilla Extract Enhances the sweetness with warm, aromatic notes.
- 1 ¼ cups All-Purpose Flour Use a 1:1 gluten-free flour blend if needed.
- ½ tsp Baking Powder Helps the cookies rise slightly.
- ¼ tsp Salt Balances sweetness and enhances flavors.
Topping Ingredients
- ½ cup Brown Sugar Caramelizes during baking for the signature upside-down effect.
- 2 tbsp Melted Butter Helps create a rich, syrupy base.
- 1 small can Pineapple Rings, cut into smaller pieces Fresh pineapple can also be used.
- Maraschino Cherries, halved Fresh cherries or dried cranberries can be used as alternatives.
Instructions
Preparation
- In a bowl, mix softened butter, granulated sugar, and brown sugar until creamy.
- Add the egg and vanilla extract, mixing until well combined.
- Stir in the flour, baking powder, and salt until you have a soft dough.
Prepare the Topping
- In another bowl, combine melted butter and brown sugar. Mix well.
- Spread this mixture on the bottom of your cookie pan.
Assemble the Cookies
- Place small spoonfuls of cookie dough on top of the brown sugar mixture.
- Add pineapple pieces and halved cherries on top of each cookie dough mound.
Bake the Cookies
- Preheat your oven to 350°F (175°C).
- Bake for 12-15 minutes or until the edges are golden.
Serve and Enjoy
- Let the cookies cool slightly before flipping them on a plate to reveal the delicious toppings.
