the BEST pineapple upside-down cake {or how to live dangerously without leaving your kitchen}

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So after making the delicious Hawaiian Luau Teriyaki Chicken Bowls, I had a ton of leftover pineapple in the fridge. I’ve been craving pineapple upside-down cake for a couple weeks and decided that today was the day to make one.

I put my ingredients together the same way I always do, and stupidly decided at the last minute that I didn’t need to put anything under the cake pan. I just popped it in the oven, thinking correctly, that there was plenty of room for the cake to rise so why bother with a jelly roll pan or foil? Ahem. Well, as the cake baked the batter behaved but the buttery caramel that makes this cake famous proceeded to start bubbling over onto the bottom of the oven. Luckily I caught it after only a couple Tablespoons had escaped the pan, but unfortunately it wasn’t soon enough. As soon as I opened the oven our entire kitchen (and other downstairs rooms) started to fill with the thickest smoke I’ve ever seen. I’m not kidding. I’ve never seen so much smoke! If I hadn’t been in such a lather to get the blasted stuff OUT of my house I would have taken a photo for this post as a visual cautionary tale with a caption under the picture that said, “If your cake does THIS while it’s baking, you’re doing it wrong.” My husband and I ran around the kitchen like crazy people, scraping the oven, dousing the bottom with water and paper towels, turning on fans, closing doors…. Ugh. I was a little worried that by the time we got the cake back into the oven it would be ruined or refuse to rise. As the haze subsided, I lined the rack with foil, put the cake back in the oven, closed the door, turned on the timer for the remaining half hour, and waited. Miraculously, a half hour passed without any further disasters and without having to call the fire department. The cake came out perfect.

I hope you still want to make my cake. It really and truly is the best. I swear.

Anyhoo, after it was safely out of the oven and flipped onto a jelly roll pan I started to laugh. I thought of different things to call my post and some of the stuff I came up with cracked me up. Other than what I ended up calling the post, I thought of calling it: Pineapple Upside-Down Cake {or this cake is so damn good it just may be worth risking your life for.} I don’t know why I thought that was so funny. Smoke inhalation?

Note: Use fresh pineapple for this. It makes all the difference.

~ preheat oven to 350 degrees F. ~

1/2 cup real, unsalted butter

1 and 1/3 cup packed brown sugar

3 and 1/2 cups fresh pineapple chunks

2 and 2/3 cup all purpose flour

2 cups sugar

1 Tablespoon baking powder

1 teaspoon salt

2/3 cup vegetable oil

1 and 1/2 cups milk + 1 Tablespoon white vinegar

2 large eggs, lightly beaten

1 teaspoon pure vanilla extract

Place the butter in a 9×13 glass baking pan. Place pan in oven to melt it. Once melted, sprinkle the brown sugar evenly over the melted butter, followed by an even layer of the pineapple chunks. Set pan aside.

In the bowl of a counter top mixer, combine: flour, sugar, baking powder and salt. Mix by hand, using a wire whisk.

Add: oil, milk and vinegar mixture, eggs, and vanilla. Using the whisk attachment, mix on low for 30 seconds just to combine ingredients. Then, turn mixer to high and beat for 3 minutes, scraping down sides of bowl a couple times during the process. Pour batter into cake pan over pineapple.

Place cake pan on a jelly roll pan or line the rack with aluminum foil, for the love of all that is HOLY. 🙂

Bake for 55 to 65 minutes or just until a toothpick inserted into the center of the cake comes out with a couple moist crumbs on it. Once done, remove cake from oven. Gently loosen sides of cake from pan using a butter knife. Place a clean jelly roll pan or large rectangular platter over the cake pan and carefully flip cake over while still in pan. Allow cake pan to rest over the cake for 3 minutes prior to removing it so the the caramelized brown sugar can drizzle over the top of the cake. Serve warm, at room temperature, or cold with sweetened whipped cream and maraschino cherries.



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  25 comments for “the BEST pineapple upside-down cake {or how to live dangerously without leaving your kitchen}

  1. chris
    July 14, 2016 at 7:08 am

    Hi Melissa,
    I just printed this recipe and will make it this weekend. I cracked up reading how the cake bubbled over and how you and your husband were running around the kitchen. I have had similar situations but thanks for sharing that so I will remember to put something underneath it. I love your posts. 🙂

    • Melissa
      July 14, 2016 at 9:04 am

      Hi Chris 🙂
      I’m glad you enjoyed the post. It was one of those situations that wasn’t funny at the time, but then about 10 minutes after the smoked cleared I was laughing. Just when you think you’re a master in the kitchen, something like this happens to humble you. Hee hee 😉 Enjoy the cake!

  2. July 16, 2016 at 2:16 pm

    i love pineapple upside down cake, thinking of making this today. You said to use fresh’ do you think frozen pineapple would work?

    • Melissa
      July 16, 2016 at 5:10 pm

      Hi Nancy,

      Frozen pineapple should work as long as you thaw it completely and blot it dry. Hope that helps! ~M 🙂

  3. Sundee
    July 17, 2016 at 7:11 pm

    Is it ok to use canned pineapples?

    I work in a preschool and feed about 100 children a day. I would love to make this for them. Could you help me adjust the recipe to feed this many.
    Thank you.

    • Melissa
      July 17, 2016 at 9:45 pm

      Hello Sundee 🙂
      You can use canned pineapple, just make sure to drain it very well. My recipe will feed approximately 12, so I would say you’d have to make 5 cakes to feed 100. Hope that helps! ~Melissa

  4. rachel
    October 4, 2016 at 4:01 am


    Quick question. How necessary is a glass baking dish?

    Thanks! – rachel

    • Melissa
      October 4, 2016 at 5:19 pm

      Hi Rachel 🙂
      I use glass baking dishes almost exclusively. You can use whatever pan you have, but I like glass.


  5. Ping
    October 11, 2016 at 6:00 pm

    Cracked me up! ????
    I know mine will never turn out the same unless I go thru every single step u did … Haha! I’d call it Smoked Upsidedown Pineapple Cake. But it certainly looks yummy. I will try that real soon. Thanks for sharing!

    • Melissa
      October 12, 2016 at 9:59 am

      Hi Ping! 🙂 Yeah, it was funny after the fact. lol. So happy you like the recipe. Thanks for stopping by! Enjoy ~M

  6. Joy
    October 14, 2016 at 6:26 am

    At what temperature did you bake it at?

    • Melissa
      October 14, 2016 at 10:35 am

      350 degrees F. As the recipe indicates…

  7. October 15, 2016 at 4:49 pm

    Hey, I cheated and used a yellow cake mix with pudding. I melted a stick of butter, the juice of the canned pineapple, and brown sugar and let it cool. The mix, 3 eggs, 1/3 cup of room temp butter, and a cup of my cooled mixture. Mixed well. Lined pineapple halved slices in the bottom of bunds pan, pour alittle of my me mixture around the slices then gently poured the cake batter around. Cooked 350 for 42 minutes. Checked by sticking in a knife and it came out clean. Let cool so I could handled the bundt pan for plate cover flipping out. Wa ya it came out perfect. It is so moist and tender. Don’ t know why I fixed it this way for the first time but I will write this down so I can remember to do it this way again. I poured the left over mixture over the cake for more moisture.

    • Melissa
      October 16, 2016 at 4:33 pm

      That’s not cheating 🙂 Sounds FABULOUS! Thanks for sharing, Patricia! XO ~M

  8. Debbie
    October 15, 2016 at 10:42 pm

    Looks fabulous! I’ve made many, and have never used fresh pineapple before! That just sounds out of this world!

    • Melissa
      October 16, 2016 at 4:33 pm

      Thanks, Debbie! 🙂 Enjoy the recipe, and thanks so much for stopping by. XO ~M

  9. Cathy
    October 16, 2016 at 12:16 pm

    Hi, my mom taught me to just take a box of salt and sprinkle some of it over a spill as soon as you see/smell it . It will stop most of the smoking so your food can finish cooking. Then let you oven cool down a bit, scrape the burned food off , wipe the salt out with a damp cloth as you are cleaning the oven.

    • Melissa
      October 16, 2016 at 4:32 pm

      Great tip, Cathy! Thanks for sharing 🙂

  10. Vicky
    January 22, 2017 at 6:56 am

    Hi, are the measurements American or British?

  11. March 10, 2017 at 9:32 pm

    This is thee best pineapple upside down recipe yet! I’ve made this a few times and it’s a hit in our home!! I did substitute Bulgarian Buttermilk for the milk with vinegar and it makes for a super dense cake! Thanks for sharing!

    • Melissa
      March 12, 2017 at 10:35 am

      YUM!!! Thanks so much for letting me know! XO ~M 🙂

  12. Erin McG
    March 12, 2017 at 2:06 pm

    Trying this today for my dad’s birthday.

  13. Tammy J.
    October 29, 2017 at 9:21 pm

    I made this today. It not only smells amazing while baking, but it’s so easy to put together. It tastes so very good, and not too sweet. This will be my go to cake!

    • Melissa
      November 2, 2017 at 1:40 pm

      I’m so pleased you like it 🙂 Yay! Thanks for letting me know, Tammy!

  14. T. Green
    January 29, 2018 at 9:19 pm

    Hi, I made this tonight exactly as directed w/ the exception of adding in some jarred cherries with the fresh pineapple. It turned out great…except that when I flipped it & let it sit for 4 minutes when I removed the glass pan one section flipped (tear) but I was able to flip it back over w/ a spatula & kind of mashed it back together. Some of the browned sugar also stayed in the pan which I happily scraped back onto the cake top. The kids are super excited & it is very moist.

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