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Pineapple Upside Down Sugar Cookies

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:

Pumpkin cheesecake
5 Pumpkin Desserts for Thanksgiving

Discover what favorite pumpkin desserts should be at your Thanksgiving table this year

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

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!
4.60 from 75 votes
YouTube video
Prep Time 20 minutes
Cook Time 25 minutes
Total Time 45 minutes
Course Dessert
Cuisine American
Servings 13 cookies
Calories 519 kcal

Ingredients
  

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

Instructions

  • 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. 

Nutrition

Calories: 519kcalCarbohydrates: 73gProtein: 4gFat: 23gSaturated Fat: 14gCholesterol: 86mgSodium: 283mgPotassium: 188mgFiber: 1gSugar: 49gVitamin A: 775IUVitamin C: 5.4mgCalcium: 66mgIron: 1.8mg

(Nutrition facts are an estimate and not guaranteed to be accurate. Please see a registered dietitian for special diet advice.)

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31 Comments

  1. To dry, sticks to the pan? Not mine. I used a large muffin pan to start with and used muffin liners. No worries, ya just take the liners off ,put it in a plate, warm in the microwave for 10-15 seconds and make sure nobody is around, you're going to wanna put yer face in the plate. They're that good! Thank you Miz Miranda for sharing with everyone. They're so delicious.4 stars

  2. I like this better than the cake method. The only thing I changed was using crushed pineapple instead of the rings, same but different. The cookie alone was great, I will hold on to the recipe and use it for other dessert treats.5 stars

  3. I want to make these with the granddaughters but I will be pressed for time. Do you think they would turn out if I made pre-bought cookie dough?

  4. THESE PINEAPPLE UPSIDE-DOWN COOKIES ARE AMAZING!!!!!!!! I can't say it enough. Thank you for such an awesome recipe!!!5 stars

  5. I followed this recipe to a T and I was not happy at all it I tried this recipe and it was not good it was so dry it should have been a biscuit the top part was great but the whole bottom part was so dry if you cut the whole thing in half and just see the top that's a good thing otherwise I would never make this recipe again but thank you anyway because I'm always ready to try something new have a wonderful day and God bless

    1. So sorry your cookies came out dry. Thank you for trying the recipe and I hope you try others from my site! There are some great ones here.

  6. I made this recipe, but in a mini muffin tin instead. I used crushed pineapple and half a cherry. I layered the brown sugar/butter mix, then the cherry, then a bit of pineapple, then filled the rest of the cavity with the cookie dough, by spreading it in there with an offset knife. I cleaned up the top of the pan around each one and then baked for about 14 minutes, until the edges were golden and the brown sugar mix was bubbling out. Cooled at least 10 minutes and then flipped pan upside down and tapped the bottoms. You may need to use a butter knife to loosen the edges of the cookie first before flipping...5 stars

  7. Gonna start making these in a few minutes! Did you use a cupcake pan? Or would a cupcake pan work? If you can get back to me that would be great!
    Thanks!

  8. I tried to make these and they were horrible. They never came out of the pan, it was impossible to clean, and the cookies themselves were so bland. I'm disappointed I wasted my time and money on these.1 star

    1. Hi Alexis- I am so sorry these didn't work out well for you. If you want to give them a try again, try spraying the pan with non stick cooking spray before adding the brown sugar mix, pineapple and cherries. This should help them pop out easier. They are also easiest to unmold when they are still warm and gooey. Once they cool, they do stick more. I hope this helps!

  9. These are amazing. The dough is more like a very firm cake mix and I didnโ€™t use 3 tablespoons just a couple big scoops to fill the remainder of the cup. I used cupcake pans and they worked just fine and I baked them for 23 minutes. I will absolutely make these again and recommend them for a tea or for a fun dinner party. Yummy!

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