Pineapple Upside Down Sugar Cookie Cakes

Do you love a sweet, caramelized Pineapple Upside Down Cake? What about a tried and true light, fluffy sugar cookie? Combine the two into one perfectly portioned dessert with these quick & easy Pineapple Upside Down Sugar Cookie Cakes.

Pineapple Upside Down Sugar Cookie Cakes

You’d think with the youngest son being # 4 in our lineup of kids, I’d have remembered some things.

Like the questions.

So many questions, everything is prefaced with a ‘why?’. And the obsessions.

Oh, the things they love.

Pineapple Upside Down Sugar Cookie Cakes

On his Daddy’s side, the son’s almost 100 % Italian.

My sides more of an amalgamation, a nice way of saying that culturally and genetically from me he inherited a mixed bag of DNA.

So it was really cool this year, when he came home with his study guide for Ancient Rome.

Here I was thinking it’d be a great opportunity to talk about his heritage, and a reason for him to be excited for this test. 

Pineapple Upside Down Sugar Cookie Cakes

The only cultural/historical icon my kid is obsessed with- in the entirety of Italy- is the Leaning Tower of Pisa.

Seriously, for the first week it was the answer to ever single question I quizzed on architecture, or anything remotely in that vein.

I was ready to pull my hair out.

Luckily, this week they took a field trip to a local museum with a visiting exhibit on the subject.

What a book couldn’t do to open his eyes, actually seeing artifacts and kinda living history finally did. 

Pineapple Upside Down Sugar Cookie Cakes

Granted tonight, when I asked him to give me one of Rome’s most famous buildings, he did look me dead in the face and say ‘The Leaning Tower of Pisa’.

It only lasted two seconds before he busted out in a fit of giggles, and said The Colosseum in between fits and breaths.

I couldn’t help but laugh too, at that point. He is pretty damn funny.

Also, he couldn’t wait to tell his Nonna what he’d learned and even began asking questions about his ‘Italian-ness’- as he calls it.

Pineapple Upside Down Sugar Cookie Cakes

So these sugary sweet Pineapple Upside Down Sugar Cookie Cakes aren’t remotely Italian, but they are as unforgettable as today’s field trip.

I’m pretty obsessed with them too. Maybe not as much as our youngest and Pisa, but just about.

Pineapple Upside Down Sugar Cookie Cakes

Pineapple Upside Down Sugar Cookie Cakes are the ultimate sticky, finger lickin’, feel good dessert anytime of the year.

A soft, fluffy sugar cookie base is topped with a brown sugar sweetened, caramelized slice of pineapple with a bright, cheery maraschino cherry on top.

It may not be heritage related, or a family heirloom recipe, but it is a cookie for the ages.

Other Pineapple Treats You Might Also Enjoy:

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Pineapple Upside Down Sugar Cookie Cakes

A fluffy sugar cookie base is topped with yummy slices of caramelized pineapple with a sweet maraschino cherry on top making for a perfect handheld Summer dessert!
5 from 2 votes
Print Pin Rate
Course: Cookies, Dessert
Cuisine: American
Prep Time: 20 minutes
Cook Time: 3 hours 25 minutes
Total Time: 45 minutes
Servings: 12 cookies
Calories: 557kcal


  • 2 sticks butter, softened
  • 1 1/2 cups sugar
  • 2 eggs
  • 2 tsp vanilla extract
  • 1/2 cup sour cream
  • 3 cups flour
  • 1 tsp baking powder
  • 1 tsp cornstarch
  • 1/2 tsp salt
  • 12 slices canned pineapple
  • 12 maraschino cherries
  • 1/2 cup butter, melted
  • 1 packed cup light brown sugar


  • To the bowl of a stand mixer, add the butter and sugar. Cream together until fluffy.
  • Add the eggs, extract, and sour cream mixing until evenly combined.
  • In a medium mixing bowl, add the flour, baking powder, cornstarch, and salt. Using a fork, stir together until evenly combined. While mixing on low speed, add these dry ingredients to the wet, slowly, just until you've added it all and the dough's just combined.
  • In another small mixing bowl, stir together the melted butter & brown sugar until evenly combined.
  • Lightly spray a cupcake pan with non stick spray. Add a tablespoon of the brown sugar mixture to the bottom of each cavity. Spread it slightly to cover the bottom. Add the pineapple slice on top of the brown sugar and the cherry in the center of the pineapple.
  • Add about 3 tablespoons of dough to each cavity, using a spatula or the back of a spoon to flatten/spread it out evenly.
  • Bake the cookies at 350 degrees for 25 minutes, or until the edges are golden brown and the brown sugar is bubbling up the sides. Remove the pan from the oven, and let rest for 10 minutes.
  • One by one, turn the cookies out onto a wax paper covered surface. If a pineapple slice sticks to the pan, just pick it up and reposition it onto the cookie cake.
  • Let the cookie cakes cool completely before serving & enjoying!


Recipe adapted from Cookie Dough & Oven Mitt


Calories: 557kcal | Carbohydrates: 78g | Protein: 5g | Fat: 26g | Saturated Fat: 16g | Trans Fat: 1g | Cholesterol: 93mg | Sodium: 324mg | Potassium: 194mg | Fiber: 2g | Sugar: 53g | Vitamin A: 837IU | Vitamin C: 5mg | Calcium: 68mg | Iron: 2mg


8 thoughts on “Pineapple Upside Down Sugar Cookie Cakes

  1. 5 stars
    I haven’t made these but the recipes looks wonderful!!! I plan to make these for my daughter’s shower. How many cookies does this recipe make?

  2. 5 stars
    I haven’t made these but the recipes looks wonderful!!! I plan to make these for my daughter’s shower. How many cookies does this recipe make?

    1. I haven’t frozen them. As for storing, let the cookies cool completely and then place them in an airtight container. If doing a double layer, put a sheet of parchment paper or wax paper between the layers to prevent sticking. Seal the lid, and they can sit on the counter- best eaten within 2-3 days.

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