Pineapple Upside Down Sugar Cookies
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These Pineapple Upside Down Sugar Cookies are a fun twist on the classic cake. Each oversized sugar cookie is baked with a pineapple ring, maraschino cherry, and a buttery brown sugar topping that caramelizes as the cookies bake. Once they’re flipped out of the pan, all that gooey brown sugar goodness soaks into the sugar cookie.
The sugar cookie base is soft and thick thanks to the addition of sour cream and cornstarch. Pair that with the juicy pineapple, cherry center, and buttery brown sugar topping and you basically have an individual pineapple upside down cake disguised as a cookie. And I’m perfectly okay with that!
The flavors of the cookie scream summer, but you can make this recipe any time you want especially since it is a sugar cookie! The pineapple is canned, as are the cherries, so no worries about things needing to be in season. I also used my USA Pan mini round cake pan 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 of 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. So, what could take the place of cake?
I’m a fan of cookies. Who would have guessed? I especially love sugar cookies with a thick layer of vanilla frosting and all of the sanding sugar that can stick to said frosting. They could easily replace the cake! After several days of recipe testing, I have the pineapple upside down sugar cookie recipe.
Why You’ll Love This Recipe
- Each cookie gets a whole pineapple ring and maraschino cherry!
- The brown sugar and butter create a gooey, caramelized topping.
- They’re large enough to serve as individual desserts.
- No decorating or frosting is needed.
- They’re a fun spring and summer dessert, but I’ve been known to make pineapple cookies whenever the mood hits.
Ingredient Notes
See the recipe card at the bottom of the post for all ingredients and quantities.
Butter – You’ll need softened butter for the sugar cookie dough and melted butter for the brown sugar topping.
Granulated Sugar – Creaming the sugar and butter helps create a fluffy sugar cookie.
Sour Cream – This ingredient makes these cookies different from a traditional sugar cookie. I love a sour cream sugar cookie because the sour cream adds moisture and helps create a soft, tender cookie that works well with the pineapple topping.
All-purpose Flour – Measure your flour carefully so you don’t end up with dry cookies. Do this by aerating the flour by scooping it with your measuring cup and dumping it out 3 to 4 times before doing the final scoop.
Cornstarch – Helps give the sugar cookies a soft, tender texture.
Pineapple Slices – I used canned pineapple rings so they’re all the same size. You’ll need 13 rings.
Brown Sugar – I used light brown sugar, but dark brown sugar will work really well too. The sugar melts during baking and creates the gooey topping.
The Pan Matters for This Recipe
Unlike traditional sugar cookies, these aren’t baked on a cookie sheet. That’s because the butter and brown sugar base that will be the topping after the cookies are baked needs to be baked in a pan with sides to prevent it from spreading all over the baking sheet.
This is where a mini round cake pan with individual cavities that are large enough to hold a pineapple ring comes in handy. The pan I recommend and use has measurements of 4.25 (top diameter) x 3.75 inches (base diameter) x 1.5 inches (depth) per cake cavity.
How to Make Pineapple Upside Down Sugar Cookies
Step 1: Beat the softened butter and granulated sugar until light and fluffy.
Step 2: Add the eggs, vanilla, and sour cream and mix until combined.
Step 3: Mix in the flour, baking powder, cornstarch, and salt just until the cookie dough comes together.
Step 4: In a separate bowl, stir the melted butter and brown sugar together until combined.
Step 5: Add about 1 tablespoon to the bottom of each cavitiy in your mini round cake pan and spread it into an even layer.
Step 6: Place on drained pineapple dring over the brown sugar mixture and add a maraschino cherry to the center of each pineapple ring.
Step 7: Scoop 3 tablespoons of cookie dough over each pineapple ring and use an offset spatula or the back of a spoon to gently spread the dough into an even layer.
Step 8: Bake at 350 degrees F for about 25 minutes or until the cookie edges are golden brown and the brown sugar mixture is bubbling around the edges.
Step 9: Let the cookies cool in the pan for about 10 minutes after baking and then flip them out onto a piece of parchment or wax paper.
How to Flip Pineapple Upside Down Cookies
This is the slightly messy part, but it’s also the exciting part.
Let the cookies rest in the pan for 10 minutes after baking. Cover your work surface with a baking sheet with wax paper or parchment paper. Carefully invert the pan so the pineapple side of the cookies will be facing up.
Some of the warm brown sugar mixture may run off the cookies when you flip them. That’s normal, which is why I recommend having something underneath them first.
If a pineapple ring sticks to the pan, don’t panic. Carefully remove it and place it right back on its cookie while everything is still warm. No one will ever know.
Tips for Best Results
- Drain the fruit. Excess pineapple juice can thin out the brown sugar topping.
- Use room temperature butter for the dough. It creams more evenly with the sugar.
- Don’t overmix the cookie dough. Once the flour is incorporated, stop mixing.
- Measure the brown sugar topping. About a tablespoon in each cavity gives you a more even amount from cookie to cookie.
- Spread the dough out evenly. This helps the cookies bake evenly and gives them a nice shape once they’re flipped.
- Don’t immediately flip the cookies. They’re very soft straight from the oven. Give them about 10 minutes to set first.
- Don’t leave them in the pan too long either. As the brown sugar cools, it can become sticky and make the cookies harder to release.
- Protect your work surface. That warm brown sugar mixture can run when the cookies are flipped. Parchment or wax paper makes cleanup much easier.
How to Store Pineapple Cookies
Once the cookies have cooled completely, store them in an airtight container. They’re best eaten within 2 to 3 days.
Because these cookies contain moist fruit on top, I wouldn’t stack them directly on top of one another. Place a piece of parchment or wax paper between layers if you need to stack them.
I haven’t tried freezing them, but I don’t think it would be a great idea.
This post was originally published August 25, 2017, but is being updated with new photos and more information.
If you try this recipe, be sure to leave a rating below and also share it on Instagram, and tag me! You can also find me on Facebook and stay up to date on recipe releases by joining the Newsletter!
Pineapple Upside Down Sugar Cookies
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Ingredients
- 1 cup butter, room temperature
- 1 1/2 cups granulated sugar
- 2 large eggs
- 2 teaspoons vanilla extract
- 1/2 cup full-fat sour cream
- 3 cups all-purpose flour
- 1 teaspoon baking powder
- 1 teaspoon cornstarch
- 1/2 teaspoon salt
- 13 canned pineapple slices
- 13 maraschino cherries
- 1/2 cup butter, melted
- 1 cup light brown sugar, packed
Instructions
- Preheat the oven to 350 degrees. Set aside the USA pan mini round cake pan.
- In a large mixing bowl, add the butter and sugar and beat with a hand mixer on medium speed until light and fluffy.
- Add in the eggs, vanilla extract, and sour cream. 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 to 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-tablespoon cookie scoop of cookie dough to the top. Using an angled spatula, flatten out the dough.
- Place into the preheated 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.
Video
Notes
Nutrition Info
(Nutrition information is automatically calculated, so should only be used as an approximation.)
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.
So wonderful to hear you had such great success and loved the cookies!
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.
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?
Yes! premade sugar cookie dough would definitely work and help save some time.
THESE PINEAPPLE UPSIDE-DOWN COOKIES ARE AMAZING!!!!!!!! I can’t say it enough. Thank you for such an awesome recipe!!!
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
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.
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…
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!
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.
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!
These are amazing. The dough is more like a very firm cake mix and I didnβt 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!
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