• Skip to primary navigation
  • Skip to main content
  • Skip to primary sidebar
The Baking ChocolaTess
  • Desserts
    • Bars
    • Blondies
    • Brownies
    • Cakes
    • Cheesecakes
    • Cobblers and Crisps
    • Cookies
    • Cupcakes
    • Pies
    • Poke Cakes
    • Trifles
  • Holiday Seasonal Desserts
    • Roundups
    • Birthday & Sprinkle Fun
    • Halloween
    • Thanksgiving
    • Christmas
    • New Years
    • Valentine's Day
    • St. Patrick's Day
    • Easter
    • 4th of July
    • Mother's Day
    • Father's Day
    • Candy Included
    • Jello Shots
    • Party Desserts
  • No-Bake Dessert Recipes
    • Cereal Treats
    • Dips & Cookie Doughs
    • Fillings
    • Frostings
    • Fudges
    • Ice Cream & Frozen Desserts
    • Layered Desserts
    • Puddings
    • Truffles
  • Breakfast & Brunch
    • Breads
    • Coffee Cakes
    • Donuts
    • Muffins
    • Rolls
    • Smoothies
  • Healthy Sweets
    • Gluten-Free
    • Flourless
    • Keto
    • Sugar-free
    • Vegan
  • Favorite Flavors & Ingredients
  • Videos
    • Amazon Shop Baking Supplies
  • Nav Social Menu

    • Facebook
    • Instagram
    • Pinterest
    • Twitter
    • YouTube
menu icon
go to homepage
  • RECIPES
  • VIDEOS
  • BAKING 101
  • ABOUT
  • SUBSCRIBE
    • Facebook
    • Instagram
    • Pinterest
    • Twitter
  • search icon
    Homepage link
    • RECIPES
    • VIDEOS
    • BAKING 101
    • ABOUT
    • SUBSCRIBE
    • Facebook
    • Instagram
    • Pinterest
    • Twitter
  • ×

    Home » Recipes » Cakes

    Fresh Pineapple Upside Down Cake

    Published: May 6, 2018 · by Kim Lange · This post may contain affiliate links ·

    1.1K shares
    • Facebook
    • Twitter
    • Yummly
    Jump to Recipe Print Recipe
    Ultimate Fresh Pineapple Upside Down Cake
    Ultimate Fresh Pineapple Upside Down Cake
    Ultimate Fresh Pineapple Upside Down Cake
    Ultimate Fresh Pineapple Upside Down Cake
    Ultimate Fresh Pineapple Upside Down Cake

    This Ultimate Fresh Pineapple Upside Down Cake has caramelized fresh pineapple basking in a rich butter brown sugar gooiness atop a fluffy vanilla cake.  So much caramelized yumminess, it's insane.

    Developed centuries ago, this classic cake has stood the test of time. 

    • These cakes used to be cooked in cast iron skillets over an open fire.
    • Then, fruit and sugar was added to the bottom of the skillet and cake batter was poured over the mixture.
    • Once cooked, flipping it over onto a plate not only released the cake from the skillet, but showed how pretty the caramelized fruit was on top.  Ta-dahhhh!

    This awesome pineapple cake deserves to be put on a pedestal. 😉 

    Ultimate Fresh Pineapple Upside Down Cake

    This delicious dessert consists of a fluffy white vanilla cake made with fresh pineapple, brown sugar and butter for the caramelization.

    But of course, if you don't have fresh pineapple, you can absolutely use canned pineapple. I had a fresh pineapple on hand I bought at the grocery (ALDI) and have wanted to make this vintage recipe to put on the blog, so here we are.

    Finally getting to it.  There's like a million desserts I want to make, but this is one I definitely wanted to share with you.

    Use Any 8 Inch Baking Pan that isn't a Springform Pan

    • Lesson learned!  When you make these types of upside down cakes, Once things start heating up, that glorious butter brown sugar glaze is going to drip and spill in your stove and make a huge mess in your oven.  Then you'll probably be mad at me.  So I'm letting you know it's best not to use a springform pan if possible. 🙂
    • Bake it in a regular 8" buttered cake pan to get ultimate results.

    I LOVE the Classic Desserts!

    With this dessert recipe, you basically cook the fruit with the butter and brown sugar until tender and then place it in the bottom of your pan.  Make and dollop the cake batter on top and then smooth out.  Bake away! Leave to stand for 5 minutes then turn out onto your platter.

    Speaking of classic, you'll love this Heavenly Hash Pineapple Fluff Dessert too!

    Ingredients You Need

    Bottom of Cake

    • brown sugar

    Caramelized Fresh Pineapple

    • brown sugar
    • unsalted butter 
    • 1 large pineapple—peeled quartered, cored and sliced ⅓ inch thick (You may want to cut the pineapple up smaller if you want smaller chunks.)

    Vanilla Cake

    • unsalted butter 
    • granulated sugar
    • Greek yogurt or sour cream
    • eggs
    • vanilla extract
    • all-purpose flour
    • baking powder
    • baking soda
    • salt

    How to Make Pineapple Upside Down Cake

    Pan Preparation

    1. Preheat the oven to 350°.
    2. Butter a deep dish 8-inch or 9-inch round cake pan. Sprinkle the bottom with 2 tablespoons of the brown sugar.

    Caramelized Fresh Pineapple

    1. In a large skillet, combine ¾ cup of brown sugar with ½ stick of butter and cook over moderately low heat until the butter is melted. Add the pineapple and cook over moderately low heat, stirring occasionally, about 20 minutes or pineapple is tender. Using a slotted spoon, arrange the slices in the cake pan, overlapping them if necessary, then pour the pan juices over the pineapple, set aside.

    Vanilla Cake

    1. In a medium bowl, whisk together the flour baking powder, baking soda and salt, set aside.
    2. In a large bowl, whisk together yogurt, eggs, vanilla, set aside.
    3. Using mixer, mix together the softened butter and sugar for 2 minutes on medium speed and then add in the yogurt/egg mixture and mix together.
    4. Add flour mixture to the yogurt mixture and mix just until combined and no lumps appear.
    5. Spoon the batter over the pineapple and spread it evenly.
    6. Bake for about 40 minutes, until the cake is deep golden. Let cool for 5 minutes on a rack. Run a knife around the edge of the cake, invert it onto a plate and remove the pan.Replace any pineapple that may have stuck to the pan. Serve warm or at room temperature.

    Serve warm or room temp.  We love fresh whipped cream with cherries with ours, but you could add a yummy scoop of vanilla ice cream and caramel topping, whipped cream and a cherry to delight in the Absolute Ultimate Fresh Pineapple Upside Down Cake treat.

    You may want to try this Pineapple Express Margarita too! 🙂  Let's Party!

    More Cake Classics!  

    • Super-Moist Chocolate Cake with Chocolate Buttercream Frosting
    • Ultimate Carrot Cake
    • Pumpkin Magic Custard Cake
    • Decadent Red Wine Chocolate Cake
    • "American Beauty" Retro Red Velvet Cake
    • Streusel Coffee Cake Pound Cake
    • Dark Chocolate Texas Sheet Cake
    • Super-Moist Vanilla Cake with Vanilla Buttercream Frosting
    Ultimate Fresh Pineapple Upside Down Cake

    Ultimate Fresh Pineapple Upside Down Cake

    Kim Lange
    This Ultimate Fresh Pineapple Upside Down Cake has caramelized fresh pineapple basking in a rich butter brown sugar gooiness atop a fluffy vanilla cake and it's INSANE!
    3.89 from 34 votes
    Print Recipe Pin Recipe
    Course Dessert
    Servings 12 Slices
    Calories 157 kcal

    Ingredients
      

    Bottom of Cake:

    • 2 Tablespoons brown sugar

    Caramelized Pineapple:

    • ¾ cup brown sugar
    • ½ stick unsalted butter softened
    • 1 large pineapple—peeled quartered, cored and sliced ⅓ inch thick (You may want to cut the pineapple up smaller if you want smaller chunks.)

    Vanilla Cake

    • 1 stick (½ cup) unsalted butter very softened
    • ¾ cup granulated sugar
    • ½ cup Greek yogurt or sour cream
    • 2 large eggs
    • 1 teaspoon vanilla extract
    • 1 ¼ cups all-purpose flour
    • ½ teaspoon baking powder
    • ¼ teaspoon baking soda
    • ½ teaspoon salt

    Instructions
     

    • Pan Preparation:
    • Preheat the oven to 350°.
    • Butter an deep dish 8-inch or 9-inch round cake pan. Sprinkle the bottom with 2 tablespoons of the brown sugar.

    Carmelized Pineapple:

    • In a large skillet, combine ¾ cup of brown sugar with ½ stick of butter and cook over moderately low heat until the butter is melted. Add the pineapple and cook over moderately low heat, stirring occasionally, about 20 minutes or pineapple is tender. Using a slotted spoon, arrange the slices in the cake pan, overlapping them if necessary, then pour the pan juices over the pineapple, set aside.

    Vanilla Cake:

    • In a medium bowl, whisk together the flour baking powder, baking soda and salt, set aside.
    • In a large bowl, whisk together yogurt, eggs, vanilla, set aside.
      Using mixer, mix together the softened butter and sugar for 2 minutes on medium speed and then add in the yogurt/egg mixture and mix together.
      Add flour mixture to the yogurt mixture and mix just until combined and no lumps appear.
    • Spoon the batter over the pineapple and spread it evenly.
    • Bake for about 40 minutes, until the cake is deep golden. Let cool for 5 minutes on a rack. Run a knife around the edge of the cake, invert it onto a plate and remove the pan.
    • Replace any pineapple that may have stuck to the pan. Serve warm or at room temperature.

    Notes

    Canned pineapple can be used as well.

    Nutrition

    Calories: 157kcalCarbohydrates: 38gProtein: 1gFat: 1gSaturated Fat: 1gSodium: 125mgPotassium: 49mgFiber: 1gSugar: 28gCalcium: 22mgIron: 1mg
    Keyword cake, pineapple, summer desserts, vanilla cake
    Tried this recipe?Let us know how it was!
    « Orange Cream Glazed Pound Cakes
    30 Mother's Day Desserts for Mom! »
    1.1K shares
    • Facebook
    • Twitter
    • Yummly

    About Kim Lange

    Hi! I'm Kim! As you may know, I'm cookie, brownie and chocolate obsessed! You'll find hundreds of decadent and healthy dessert recipes to choose from here! So, let's bake something easy and never forget the chocolate!

    Reader Interactions

    Comments

    1. jo says

      August 26, 2020 at 4:17 am

      Aloha Kim,
      I specifically sought out to find a recipe that used fresh pineapple rather than canned since I prefer fresh, and it's what I had on hand. Thank you for taking the time to create and share this recipe. Yours is hands-down, the MOST delicious pineapple upside down cake I've ever had! This is my first time making one (my husband requested pineapple upside down cake for his birthday this year), yet it was simple to make, and we both really enjoyed it. I would make this recipe again 🙂

      • Kim Lange says

        August 27, 2020 at 3:40 pm

        That is wonderful to hear Jo! I'm so happy you all enjoyed it for your husband's birthday! Tell him 'Happy Birthday' from me and thank you so much for trying it!! xo

    2. Kelly @ Kelly Lynns Sweets and Treats says

      June 18, 2020 at 9:26 am

      Love pineapple upside down cake! This looks so yummy. Pinning!

      • Kim Lange says

        June 18, 2020 at 10:19 am

        Thank you so much!

    3. Carole Pipolo says

      June 12, 2020 at 9:33 am

      My husband of 50 years always like me making a pineapple upside down cake, but I've never made one with fresh pineapple, but today is the day after finding this recipe. I'm giving you five stars without even a taste as I am quite impressed with your technique. So here goes. Will mark your blog and see what else you have going on. Thanks.

      • Kim Lange says

        June 12, 2020 at 12:20 pm

        Thank you so much Carole! You are so sweet! I hope you find lots of goodies! xo

    4. Cindy says

      October 07, 2019 at 7:25 pm

      Hi, I'm just about finished baking, but the center is still wobbly after 40 minutes so ive put it back in for another 10. Is this a mistake? Not sure how these cakes bake.

      • Kim Lange says

        October 08, 2019 at 7:12 am

        No the center should not be wobbly, so it's good that you put it back in the oven. It should be firm on top. I hope it worked out for you after putting it back in the oven Cindy.

      • BRANDY says

        December 31, 2019 at 5:48 pm

        Thanks Kim! I'm getting ready to make this now for a lunch get together at my dad's tomorrow. I was worried I was missing something. Recipe looks delicious and I can't wait to try it. I am in charge of dessert and wanted to make something with stuff I already had on hand. I found your recipe because I also had a pineapple from Aldi that I needed to use. Lol! This looks so much better than the overly sweet recipes using canned pineapple. I also love that the cake is from scratch and not a box mix since I never purchase those so none sitting around.

    5. Sherry says

      March 02, 2019 at 11:27 am

      This is one of the best recipes I have ever found! The carmelization ofthe pineapple is key! Thank you soooo much for sharing! Yummy!!!!

      • Kim Lange says

        March 03, 2019 at 3:04 pm

        Great to hear Sherry. I'm so happy you found it,tried it and loved it. 🙂 Thanks so much.

    6. SJ Murray says

      December 26, 2018 at 5:56 pm

      Hi, I’m making this cake today, very excited to try it! Would you please share what the measurements are for 1 stick and 1/2 stick of butter?
      Thanks & regards Sarah-Jane

      • Kim Lange says

        December 27, 2018 at 9:43 am

        Hi Sarah-Jane! It would be 1 & 1/2 cups of butter. Hope you enjoy!

    7. Linda says

      December 15, 2018 at 12:39 pm

      I’ll use a 9” pan next time. The 8” makes a mess

    8. Sherry says

      July 04, 2018 at 3:28 pm

      I have made some awesome recipes from Pinterest, but this one is the bomb!! The pineapple is to die for and the cake truly is insane! So glad I found you! Thank you for this incredibly yummy recipe!

      • ChocolaTess says

        July 04, 2018 at 7:29 pm

        So glad you enjoyed it Sherry! Thank you so much!!

    9. Ravonda says

      May 14, 2018 at 7:05 pm

      This turned out quite well. I was concerned that it could stick, so despite the warning not to use a springform pan, I went that direction anyway, but lined it with parchment paper and it worked beautifully. I followed the recipe except that I chopped my pineapple quite small before carmelizing.

      I loved the way you decorated it and did the same. The piped whipping cream gives it a wow factor and complements the cake well.

      This was a really good cake! Love that it uses fresh pineapple and isn’t a huge cake.

      • ChocolaTess says

        May 14, 2018 at 8:22 pm

        I'm so thrilled you enjoyed it Ravonda! I like the idea of cutting up the pineapple smaller like you did or even crush it up a bit for a different texture. Thank you so much for being so sweet!

    10. heather (delicious not gorgeous) says

      May 08, 2018 at 10:45 pm

      yessssss. i'm in love with upside down cakes and all that delicious gooey caramel <3

    11. Liz says

      May 08, 2018 at 9:51 am

      These are the times I wish my hubby liked pineapple. This was one of my dad's favorites--wish I could make it for him <3 Yours is gorgeous!!

      • ChocolaTess says

        May 08, 2018 at 2:32 pm

        Aww thank you Liz! 🙂

    12. Katherine I LOVe in my oven says

      May 07, 2018 at 10:20 pm

      That caramelization!!! Yum! This isn’t something I’d think to make, but now it will be!!

      • ChocolaTess says

        May 07, 2018 at 10:29 pm

        Thank you Katherine! 🙂 So happy for you btw! Mama of 3!

    13. [email protected] says

      May 07, 2018 at 10:50 am

      This is one of our all-time favorite cakes! That caramelization is everything!! Pretty photos, my friend! 🙂

      • ChocolaTess says

        May 07, 2018 at 12:22 pm

        thank you so much Annie!! 🙂

    14. Kelsie | the itsy-bitsy kitchen says

      May 06, 2018 at 9:27 pm

      The word ultimate says it all. This looks simply incredible! Two slices for me please!

      • ChocolaTess says

        May 07, 2018 at 12:28 pm

        Thank you and yes 2 slices for you!! 🙂

    15. Maria | kitchenathoskins says

      May 06, 2018 at 9:21 pm

      I love the use of fresh pineapple Kim. To be honest, I'm not a huge fan canned fruits and veggies. This is certainly a delicious classic and I so love the pretty pictures:)

      • ChocolaTess says

        May 07, 2018 at 12:30 pm

        Thank you so much Maria! I love using the fresh fruits as much as possible too!

    16. leanne | Crumb top baking says

      May 06, 2018 at 8:37 pm

      This is truly the real deal Kim! Love that caramelization! I've never made a pineapple upside down cake, but now it is definitely on my list! Thanks for an awesome recipe!

      • ChocolaTess says

        May 07, 2018 at 12:31 pm

        Omgosh, I forgot how much I loved this cake Leanne! It's definitely a keeper!! I hope you try it!

    Trackbacks

    1. 45+ Awesome Easter & Spring Desserts – The Baking ChocolaTess says:
      December 29, 2020 at 10:48 am

      […] Ultimate Fresh Pineapple Upside Down Cake […]

    2. 30 Mother’s Day Sweet Ideas says:
      May 8, 2018 at 8:54 pm

      […] Ultimate Fresh Pineapple Upside Down Cake – Ultimate Fresh Pineapple Upside Down Cake!  So much caramelized yumminess, it’s insane.  Mom wants! […]

    Primary Sidebar

    WELCOME!

    Kim Lange

    Hi, I'm Kim! As you may know, I'm cookie, brownie and chocolate obsessed! You'll find hundreds of decadent and healthy dessert recipes to choose from here! So, let's bake something easy and never forget the chocolate!

    More about me →

    CATEGORIES


    POPULAR

    • Perfect Banana Chocolate Chip Muffins! Fluffy & Moist!
    • Soft Batch Chocolate Chip Cookies! Pure Nirvana
    • Awesome Country Apple Fritter Bread
    • Perfect Chocolate Chip Cookies
    • Homemade Snickerdoodle Cookie Bars
    • "Phenomenal" Milk Chocolate Chip Peanut Butter Cookies

    AS SEEN IN

    BRANDS TBC

    Footer

    ↑ back to top

    Info

    • About
    • Recipe Index
    • Contact
    • Work With Me
    • Privacy Policy

    Contact

    • [email protected]
    The Baking ChocolaTess Blog

    Follow

    • Facebook
    • Pinterest
    • Instagram

    Copyright © 2023 THE BAKING CHOCOLATESS