Pineapple upside down sugar cookies are the perfect summer treat and after that tasty pineapple and cherry are gone, you still have a soft, fluffy sugar cookie! These are easy to pick up and eat, but can leave you slightly sticking from all of that buttery brown sugar glaze.
pineapple upside down sugar cookies on a white table with brown sugar

Pineapple Upside Down Sugar Cookies

Summer isn’t quite over and I want to get the rest of my summer ideas out before it’s too late. I’ve been sort of taking it easy since this summer has been C-R-A-Y! Between intense cookie cookbook creating, my kiddo being home, and a new 1-year-old pitbull who is as stubborn as I am, I’m struggling. I could probably write an entire novel on my struggles right now. I’m tired and want a hugeee pity party for myself, but I’ll spare you. You are so welcome!

The flavors of the cookie are totally summer, but you can make this recipe any time you want! The pineapple is canned as well as the cherries, so no worries of things needing to be in season. I also used my USA Pan mini round cake pan (aff. link) that I used in my Christmas tree cake post. It’s always nice to have multiple uses for a pan!

overhead of pineapple upside down sugar cookies

Let me tell you how I came up with this recipe! I’m a toppings girl. I will eat all of the toppings off from anything whether it’s pineapple upside down cake, monkey bread, or pizza. Then after I eat the toppings off of the pineapple upside down cake, I’m left with a plain yellow cake that I don’t particularly love without frosting. I know the consequences before eating the toppings, but this girl just can’t help herself. Well, I’m a fan of cookies. Hence, the cookie cookbook coming out SOON. Plus, there is less cookie than cake making it nearly equal portions of topping to cookie. This is where I would throw in 2 – 3 thumbs up emojis.

Other great pineapple desserts:

  • Pineapple Upside Down Skillet Cake
  • Pineapple Carrot Cake with Cream Cheese Frosting
  • No-Bake Pineapple Cream Dessert

How to make Pineapple Upside Down Sugar Cookies

Pineapple Upside Down Sugar Cookies - Pineapple upside down cake in cookie form because everyone loves cookies! Soft sugar cookie bottoms with a ring of pineapple and cherry center all covered in a brown sugar glaze!

Pineapple Upside Down Sugar Cookies

5 from 4 votes
Prep Time:20 minutes
Cook Time:25 minutes
Total Time:45 minutes
Servings: 13 cookies
Calories: 519kcal
Author: Miranda Couse
Course: Dessert
Cuisine: American
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Pineapple upside down sugar cookies are the perfect summer treat and after that tasty pineapple and cherry are gone, you still have a soft, fluffy sugar cookie!


  • 1 cup butter room temperature
  • 1 1/2 cups granulated sugar
  • 2 eggs
  • 2 tsp. vanilla extract
  • 1/2 cup sour cream
  • 3 cups all-purpose flour
  • 1 tsp. baking powder
  • 1 tsp. cornstarch
  • 1/2 tsp. salt
  • 13 canned pineapple slices
  • 13 maraschino cherries
  • 1/2 cup butter melted
  • 1 cup light brown sugar packed


  • Preheat oven to 350 degrees. Set aside the USA pan mini round cake pan.
  • In a large mixing bowl, add in the butter and sugar and mix until light and fluffy.
  • Add in the eggs, vanilla extract, and sour cream and mix until combined.
  • Add in the flour, baking powder, cornstarch, and salt. Mix until the cookie dough just comes together. Set aside.
  • In a separate bowl, stir together the melted butter and brown sugar until combined.
  • Add about a tablespoon of the brown sugar mixture into the bottom of each cavity. Spread it around to cover the bottom.
  • Add the pineapple slice on top of the brown sugar and the cherry in the center of the pineapple.
  • Add a 3 T. cookie scoop of cookie dough to the top. Using an offset spatula, flatten it out. 
  • Place into the oven and bake for 25 minutes or until the edges are golden brown and the brown sugar is bubbling up the sides. 
  • Let cool for 10 minutes and then turn out onto a wax paper covered surface. Brown sugar will run all over, so the wax paper is necessary. If the pineapple sticks to the pan, just reposition it back on the cookie.
  • Let cool completely before eating. Store in an airtight container. These are best if ate within the first 2 - 3 days. 
Keyword: Pineapple Upside Down Sugar Cookies



Calories: 519kcal | Carbohydrates: 73g | Protein: 4g | Fat: 23g | Saturated Fat: 14g | Cholesterol: 86mg | Sodium: 283mg | Potassium: 188mg | Fiber: 1g | Sugar: 49g | Vitamin A: 775IU | Vitamin C: 5.4mg | Calcium: 66mg | Iron: 1.8mg
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