Sweet and juicy, these Pineapple Upside Down Cookies are made with a soft sugar cookie base topped with a pineapple ring and maraschino cherry! They look like individual portions of the classic pineapple upside-down cake, and are perfect for any occasion!
These tasty Pineapple Upside Down Cookies are a perfect summer treat for any occasion.
Make them for a birthday party, BBQ, potluck, or summer brunch!
We all love the classic Pineapple Upside Down Cake, and here it is in cookie form.
This easy cookie recipe is so much fun to make, and as we're using canned fruit, you can enjoy them all year round!
It's a great recipe to have on hand for whipping up a dessert last minute as well, as all the ingredients will keep for ages in your pantry.
For more delicious cookies, check out my Boston Cream Pie Cookies, Lemon Cheesecake Bars, and these Blueberry Pie Cookies.
Shopping List
Wet Ingredients. Butter, Vanilla Extract, Egg, Vegetable Oil
Dry Ingredients. All Purpose Flour, Granulated Sugar, Brown Sugar, Powdered Sugar, Baking Soda, Cream of Tartar, Salt
Fruit. Canned Pineapple Slices (Rings), Maraschimo Cherries
How to Make Pineapple Upside-Down Cookies
Pan Preparations
I use a Wilton Muffin Top Pan to make all of my Cookie Pie Recipes. It's a non stick pan and the cookies will easily slide out. It's a must when making Pineapple Upside Down Cookies.
The first thing you always need to do when baking cookies is to preheat the oven. For this recipe, we'll need it at 350 F Degrees.
In a small mixing bowl combine ½ cup of melted Butter with 1 cup of Brown Sugar, and stir to combine.
Drain the Pineapple Juice from the can and set the Pineapple Rings aside.
Place 1 tablespoon of the Butter and Brown Sugar mixture into a well of the muffin tin pan and top with 1 Pineapple Ring. Then, add 1 Maraschino Cherry in the center of each Pineapple Ring.
TIP: I like to stagger the positions of the cookies in the pan allowing for cookies to spread without touching.
Cookie Dough Directions
Cream Softened Butter and Granulated Sugar together until light and fluffy scraping down the sides of the bowl as needed.
Add Egg and Vanilla extract and continue to cream for 2-3 minutes.
Gradually add Vegetable Oil and Powdered Sugar to the butter mixture and cream ingredients. The mixture will cream together and turn pale yellow in color
Add the dry ingredients of All Purpose Flour, Baking Soda, and Baking Powder to the butter mixture until fully combined.
Scoop cookie dough using a size #24 Cookie scoop.
Press cookie dough flat in the palm of your hand to be about 3 inches in diameter.
Place the flattened cookie dough on top of the pineapple ring and cherry, and carefully tuck the cookie dough into the sides of the well of the pan, sealing the edges.
Bake in the preheated oven for 8-10 minutes or until the edges are lightly golden brown and the center is no longer glossy.
Remove from the oven and flip the pan out onto a parchment-lined cookie sheet. Cookies will fall out of the pan to create the iconic upside-down pineapple dessert cookies!
Allow cookies to cool before serving.
Storage & Freezing
Storage: Store your cookies in an airtight container for up to 7 days. Cookies are best if enjoyed within 2-3 days.
Freezing: These cookies are best made fresh, as the pineapple and cherry will be a bit watery as you defrost them.
Substitutions & Variations
- Fresh fruit. I've used canned pineapple instead of fresh pineapple because to me, canned pineapple tastes sweeter, and works better for these cookies. If you try it with fresh pineapple, let me know how you get on!
- Pineapple Cookies. You can make a different version of pineapple cookies by using pineapple-flavored frosting on top of a fluffy sugar cookie, topped with a maraschino cherry. It is a different type of cookie, but still tastes delicious!
- Pineapple Cake Mix Cookies. You can use pineapple cake mix to make the cookie base if you prefer. Check out my Cream Cheese Cake Mix Cookie recipe to see how this can be done.
- Topping. Add a dusting of powdered sugar, or a dollop of whipped cream to these cookies to serve!
Pro Tips
What makes a good cookie? Does it have a soft center and crispy edges, and is it chewy? Each of these makes a great quality cookie. To make perfect cookies every time here are some pro tips.
To find out more, check out my Pro Tips Guide for making the best cookies every time!
Weighing Ingredients.
Baking is a science and adding too much or too little of any of the ingredients will alter the recipe. Weighing and measuring dry ingredients properly makes a world of difference. Investing in a kitchen scale is ideal. When a kitchen scale is not available, make sure to stir and lift ingredients before scooping them into a measuring cup.
| Volume | Ounces | Grams | |
| All Purpose Flour | 1 Cup | 4½ Ounces | 120 Grams |
| Bread Flour | 1 Cup | 4½ Ounces | 120 Grams |
| Granulated Sugar | 1 Cup | 7 Ounces | 200 Grams |
| Brown Sugar | 1 Cup | 7½ Ounces | 213 Grams |
| Confectionary Sugar | 1 Cup | 4 Ounces | 113 Grams |
Cookie Scoop.
Using a cookie scoop keeps each ball of cookie dough the same size, which is essential for ensuring even baking.
Baking Sheets.
You can use an ungreased cookie sheet if you prefer. I like to use Parchment Paper to line baking sheets or a Silicone Mat for easy cleanup.
Baking Time.
Every oven heats a little differently. I recommend doing a test batch of 1-3 cookies to test the baking time for a perfectly baked cookie before baking the remaining dough.
Cookies.
Cookies are perfectly baked when the edges are set and the centers are no longer glossy.
Cooling Rack.
Allow cookies to cool on the baking sheet for a minute or two before moving them to a cooling rack to cool completely.
- Kitchen Scale. I use this for accuracy in measuring and it's a lifesaver when it comes to consistent baking
- Wire Rack for cooling cookies. I like to have at least 2 cooling racks
- Mixing Bowls. A Large Mixing Bowl for mixing ingredients and small and medium mixing bowls for other ingredients
- Cookie Sheet. Most recipes will take 2 batches to bake. It's great to have multiple baking sheets available
- Parchment Paper or Silicone Baking Mat. Line the Cookie Sheet with parchment paper for easy cleanup and to prevent sticking.
- Cookie Scoop. A small #60 Cookie Scoop or a Medium Cookie Scoop #50 are great choices for uniform drops of cookie dough.
- Storage Container. An Airtight Container to store cookies or a Ziploc Bag works great too.
- Additional supplies. Measuring Cups and Measuring Spoons along with a silicone spatula are all helpful.
Have you tried this Pineapple Upside Down Cookie recipe?
Let me know what you thought of these cookies! Tag @bestcookierecipes on social media so I can see how great your cookies turned out! I would also love to read your comments below. Let me know what you think of these cookies. It really does help!
More Fruity Cookies Recipes
- Fruit Pizza Cookies
- Strawberry Chocolate Chip Cookies
- Strawberry Sugar Cookies
- Cranberry Bars
- Mango Oatmeal Cookies
- Strawberry Lemonade Bars
- Lemon Blueberry Cookies
- Lemon Curd Cookies
Pineapple Upside Down Cookies
Ingredients
Cookie Ingredients
- ½ cup Butter Softened
- ½ cup Granulated Sugar 100g
- 1 Egg Large
- 1 teaspoon Vanilla Extract
- ½ cup Powdered Sugar 65g
- ¼ cup Vegetable Oil
- ½ teaspoon Baking Soda
- ½ teaspoon Cream of Tartar
- 2 cups All Purpose Flour 240g
Pineapple Topping
- Pineapple Rings Drained
- Maraschino Cherries Drained
- 6 tablespoons Butter Melted
- 1 cup Brown Sugar 214g
Instructions
Pan Preparations
- Preheat the oven to 350 F Degrees.
- In a smaller mixing bowl combine ½ cup of melted Butter with 1 cup of Brown Sugar, and mix to combine.
- Drain the Pineapple Rings and set them aside.
- Place 1 tablespoon of Brown Sugar Butter mixture into a well of the muffin tin pan and top with 1 Pineapple Ring. Then, add 1 Maraschino Cherry in the center of each Pineapple Ring.
- TIP: I like to stagger the positions of the cookies in the pan allowing for cookies to spread without touching.
Cookie Dough Directions
- Cream Softened Butter and Granulated Sugar together until light and fluffy scraping down the sides of the bowl as needed.
- Add Egg and Vanilla extract and continue to cream for 2-3 minutes.
- Gradually add Vegetable Oil and Powdered Sugar to the butter mixture and cream ingredients. The mixture will cream together and turn pale yellow in color
- Add the dry ingredients of All Purpose Flour, Baking Soda, and Baking Powder to the butter mixture until fully combined.
- Scoop cookie dough using a size #24 Cookie scoop. Press cookie dough flat in the palm of your hand to be about 3 inches in diameter.
- Place the flattened cookie dough on top of the pineapple ring and cherry, and carefully tuck the cookie dough into the sides of the well of the pan, sealing the edges.
- Bake at 350 F Degrees for 8-10 minutes or until the edges are lightly golden brown and the center is no longer glossy.
- Remove from the oven and flip the pan out onto a parchment-lined cookie sheet. Cookies will fall out of the pan to create the iconic upside-down pineapple dessert cookies!
- Allow cookies to cool before serving.
Notes
- Storage: Store your cookies in an airtight container for up to 7 days. Cookies are best if enjoyed within 2-3 days.
- Freezing: These cookies are best made fresh, as the pineapple and cherry will be a bit watery as you defrost them.
Rebecca Johnston
Love these Pineapple upside down cookies warm from the oven as well as chilled. The chewy texture is fun for this cookie recipe.
Grace
I loved these Pineapple Upside Down cookies and so did my family. We love to make the cake and enjoy hot out of the oven. These cookies are a fun twist and so good.
Rebecca Johnston
I love these cookies too, truly a favorite
Sue Ringsdorf
These cookies are so creative and we loved them! Thanks for sharing, Rebecca!
Debi
I've seen these cookies all over social media and finally made them. I love the fresh pineapple flavor and they were so much fun.
Kathleen
So many great cookies! Loved this recipe, made for a friends birthday who doesn't like cake, except pineapple upside down cake, she was over the moon for these cookies!
Janelle
My Mother-in-Law LOVED these cookies! Thanks for the tasty recipe!
Rebecca Johnston
You are so welcome! It's such a fun recipe
Jules
What a fun treat! I made these cookies for a girls movie night and my friends thought I was a genius. Thank you for making me look good. We loved them!
Amy Nash
Holy moly these cookies are delicious. I'm not at all surprised since pineapple upside down is one of my favorite cake flavors, but still! I need to make these again ASAP because they are GONE!
Rebecca Johnston
I love love Pineapple upside down cake too which is why I just love these cookies too. So glad you loved them as well.
Linda Forstmann
I am wondering if I could do a smaller version, like using a mini muffin pan. I'd have to use a pineapple chunk and a cherry. I am going to make some like you have shown. They are so pretty. I also want to try the small version. could you suggest what size scoop for the dough? Also, what cook time? Thank you so much for such detailed instructions! That is unique.
Rebecca Johnston
Hi Linda! That would be a fun idea using a mini muffin pan. I'd use Tidbit pineapple as they are smaller and I might even chop them up a bit too. I'd also try using about a #60 cookie scoop (1 Tablespoon cookie dough) for starters. Bake at 350F for 10-12 minutes maybe? Honestly you will have to watch your oven as you bake them and see! Let me know how they work out. I'd love to hear.