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
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!
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
- 1 cup butter room temperature
- 1 ½ cups granulated sugar
- 2 eggs
- 2 tsp. vanilla extract
- ½ cup sour cream
- 3 cups all-purpose flour
- 1 tsp. baking powder
- 1 tsp. cornstarch
- ½ tsp. salt
- 13 canned pineapple slices
- 13 maraschino cherries
- ½ 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.
(Nutrition facts are an estimate and not guaranteed to be accurate. Please see a registered dietitian for special diet advice.)
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These sound and look so yummy! Thanks for the recipe! Sharing on Twitter. Thank you for sharing on Merry Monday! Hope to see ya next week!
Kat (The Baking Explorer) says
I love this idea so much! They look gorgeous too!
Yay! Thank you!
Pinned! These pineapple upside down cookies look so yummy. Stopping by from the #HomeMattersParty linky.
These look delish!!! Can I use a regular muffin pan for these?
I haven't tried it, but I don't see why it wouldn't work. I would recommend using less cookie dough and keep an eye on the bake time.
Ope! Now I see, just disregard the previous comment that I made a few minutes ago! Just had to scroll down a ways. Whoops!
Jocelyn (Grandbaby Cakes) says
This recipe is ingenious!! Love it!!!
Melissa Torres says
They look amazing and I'm positive they taste amazing too!
I love pineapple and what a good idea to make this recipe with sugar cookies. I love the cherry too. Thank you for sharing at Funtastic Friday and congratulations on the feature.
I can't wait to give this a try! Looks AHHmazing!
What is the name of the pan you used to make these cookies? I have different pans but, the closest I have are Whoopie pie pans.
Yeah I like to eat the toppings too! These babies are right up my alley. Besides, I go crazy for pineapple flavors.
I love this! Really fun and gorgeous!
Dianne lennon says
Where would I find the pan to make these delious looking cookies?
Hi! Here's a link to the pan I used for it. https://amzn.to/2X7le1O
Kim lovius says
These are amazing. The dough is more like a very firm cake mix and I didn’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!
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.
Miranda C. says
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!
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!
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...
Kathy L Behrens says
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
Miranda C. says
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.
THESE PINEAPPLE UPSIDE-DOWN COOKIES ARE AMAZING!!!!!!!! I can't say it enough. Thank you for such an awesome recipe!!!