Made with fresh in season pineapple, this cast iron skillet dessert is going to be a summer staple. Freshly caramelized pineapple slices dot the top of this buttery cake with crispy crumbles on top! It’s a twist on your boring old cake, this is a cast iron skillet pineapple NOT upside down cake that is for the record books!

One day it will all be funny… bring me a Jerry Seinfeld to write this story and it would be the best 30 minutes of television you have probably ever witnessed. But Saturday was not that day. Give me a week or two. Or time to allow the carpet of the baby’s room to dry, and my new iPhone X to arrive and my grandmother’s dining room tablecloth enough time to dry and it will all be hilarious.

So, 10 years maybe?

Friday Emmett had his 6 month check up. It went great by the way. His doctor said he has “fluffy” thighs (killed me dead!), said that he is the cutest baby (also true), and said he is tracking at 7-8 month development (gold star!). Then there were the shots, four of them, plus an oral. He still did stellar. I typically cry more when I get shots. And a good night sleep was had by all.

But at 4 am on Saturday morning, things started to change. I was awake, and Emmett was stirring wanting a little food. No biggie, one wake up in the night? I could handle that! But he wouldn’t go back down. I tried everything. Boob, bottle, rocking, singing (probably not the best choice), silence to ride out the tears, and then an attempt at a diaper change… when it all went terribly terribly wrong.


We are talking Exorcist style, projectile, all over me, and himself, onto the carpet, splattering onto his dresser. EVERYWHERE. I froze, took time to evaluate the situation, and just stood there, still as a tree, trying to watch my step. And as I backed away slowly, thinking through each step… “Put the kid on the changing table, change him, get the steam cleaner, take off that sweatshirt, it will be okay. Oh god the smell… then…”  IT HAPPENED AGAIN.

At that point all was lost, I gave up, it was time for reinforcements. BENNNNN!! I need help. He walked into Emmett’s room, mildly horrified, but calm, laying down two towels like they would do much to really help the situation other than moderately cover the evidence of what had just transpired. It was time to revaluate the plan. Ben, give the kid a bath, I will get the steam cleaner. And we tackled it. I stripped off my sweatshirt and threw it in the basket, got the kid undressed and we were ready to go.

I threw the whole basket into the wash, grabbed the steam cleaner, went about it all… and if you can’t see where this is going…

LIGHTS were coming out of the washer. I thought it was on fire. Bright, shining, green and pink lights. I stopped the washer immediately, opened it up and right on top, there it was. My phone, blinking it’s dying blinks of pink and green. Running into the kitchen I dropped it into the carton of rice, hoping for a miracle that would not come.

Puke everywhere, my phone dead, and a smiling and now washed baby boy lovingly be carried around by his daddy entered the kitchen. All before 7am.

And that is how I ended up at the Verizon store at 10am on the button to get a new phone. But the story doesn’t end here. No no. That would be too easy. Because when you break your phone, they won’t just simply replace it in the store. You get to all in a claim for a new one. But as luck would have it, once you do that, they will ship you a new one. But they don’t ship on Saturdays. You have to wait until Monday. So, here we are. Monday… three days without a phone. Somehow it put it into perspective how much I depended on that device for my daily everything. (At some point I may be thankful that it forced me to be more present in my daily experiences, but after shoveling out a $200 deductible on the $1200 phone, I’m not ready to acknowledge that thankfulness…)

Someone tell me this will all be funny one day.

But our day carried on much better after that. Sunday we went to visit my grandma for a birthday brunch at her house. With a baby meltdown behind us after we walked into the door, I thought we were in the clear. I bet you can guess what happens next. Among the chatter, danishes, birthday wishes and sitting on great grandma’s lap… the Exorcist emerged again. All over the tablecloth. Happy birthday grandma.

Ingredients for Cast Iron Skillet Pineapple Not Upside Down Cake

  • Flour
  • Brown Sugar
  • Butter
  • Salt
  • Freshly Sliced Pineapple Rings (from 1 Fresh Pineapple, if available)
  • Sugar
  • Baking Powder
  • Milk, or Half and Half
  • Vanilla
  • Egg Yolks
  • Dark Corn Syrup, use Light if that’s all you have

No more about me, or Emmett, or baby spits, or ruined phones – you probably only stopped by to see a skillet cake, huh? If you have made it this far, then you REALLY deserve this recipe. Pineapple upside down cake it one of my favorites, but I always depended on others to make it for me. What I adore about this Cast Iron Skillet Pineapple Not Upside Down Cake is the caramelized fresh pineapple, all fried up in a cast iron skillet until it’s just browning and getting golden. You can use as thick of slices of fresh pineapple as you want. And if you’re nervous about picking out the perfect pineapple – I CAN HELP! My how-to pick out the perfect pineapple will get you the right one every time. It’s fail proof!

Inspired Homemade Recipes To Try

Everything is better out of a cast iron skillet, and desserts especially. Try some of these other cast iron desserts below!

Blueberry Coconut Cardamom Crumble

Blueberry Coconut Cardamom Crumble

Lemon Coconut Swirl Skillet Danish 

Lemon Coconut Swirl Skillet Danish and 25 Other Insanely Delicious Cast Iron Dessert

Crepe Suzette

Crepe Suzette - Orange Crepes with Orange Butter Filling

Inspired Homemade Recipes To Try

Cast Iron Apple Pie from Your Homebased Mom

Gooey Texas Sheet Cake from The Cookie Rookie

Apple Blueberry Crisp from Rachel Cooks

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Pineapple Not Upide Down Cake in a Cast Iron Skillet on a white background with gingham napkin

Cast Iron Skillet Pineapple Not Upside Down Cake

  • Author: Country Cleaver
  • Prep Time: 15 minutes
  • Cook Time: 35 minutes
  • Total Time: 50 minutes
  • Yield: 8 servings 1x
  • Category: Dessert
  • Method: Baked
  • Cuisine: American


Made with fresh in season pineapple, this cast iron skillet dessert is going to be a summer staple. Freshly caramelized pineapple slices dot the top of this buttery cake with crispy crumbles on top!



Crumble Topping

  • 1/3 cup Flour
  • 1/4 cup packed Brown Sugar
  • 2 Tbsp Butter, softened
  • Pinch of Salt


  • 2 Tbsp Butter
  • 8 Freshly Sliced Pineapple Rings (from 1 Fresh Pineapple, if available)
  • 1 1/2 cup Flour
  • 3/4 cup Sugar
  • 1 tsp Baking Powder
  • 1/4 tsp Salt
  • 3/4 cup Milk, or Half and Half
  • 6 Tbsp Butter, softened
  • 1 tsp Vanilla
  • 3 Egg Yolks


  • 1/4 cup Brown Sugar
  • 1 Tbsp Dark Corn Syrup, use Light if that’s all you have
  • 1 Tbsp Butter
  • 1 Tbsp Lemon Juice
  • Pinch Salt



For the Topping

  1. In a bowl, blend together, using your fingers if easiest, all of the ingredients, mixing together until they become a fine crumble.
  2. Place it in the fridge to set until ready to use.

For the Cake

  1. Preheat oven to 350 degrees.
  2. In a 10-inch cast iron skillet over medium high heat, melt the butter.
  3. Once the butter is melted and beginning to bubble, lay the pineapple rings in a single layer in the skillet and allow them to begin to caramelize, about 2 minutes per side, turning over and ensuring that both sides are caramelizing.
  4. Remove them from the skillet, and set aside until ready to use.
  5. In a large bowl, whisk together the flour, sugar, baking powder and salt.
  6. Utilizing a hand held mixer, mix together the milk, butter and vanilla into the flour mixture.
  7. With the mixer on low speed, add in one egg yolk at a time, ensuring it is evenly mixed in before adding the next.
  8. Spread the batter into the cast iron skillet. Top the batter with the caramelized pineapple slices.
  9. Then lastly add in the cooled crumble topping that you created in the first step.
  10. Bake the cake for about 35 minutes, and allow to cool on a wire rack.

For the Glaze

  1. In a small saucepan, combine all the ingredients and bring to a simmer, stirring frequently until syrupy and smooth.
  2. Pour it over the cake prior to serving.


Adapted from Slow Cooker Recipes Magazine