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Pineapple Upside Down Cake For a Crowd

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Pineapple Upside Down Cake for a Crowd is the perfect cake for that upcoming family gathering. Soft, moist yellow cake with caramelized sweet brown sugar topping and sweet citrus bite of sliced pineapple and cherries. No fuss, no frosting, all flavor. Just mix it up and bake it.

Pineapple Upside Down Cake for a Crowd

Food holidays are funny, right? Like, some of them are soooo exciting. An excuse to eat more tacos and margaritas?!?! I’ll take any excuse for Carne Asada and Watermelon Basil Margs. YES PLEASE. Then some of them are super random, like National Raspberry Popover Day – not just popovers, raspberry popovers. Well, we’re putting that all aside and celebrating food days because today is National Pineapple Upside Down Cake and we’re celebrating in a big way.

By big, I mean a big ass cake. This pineapple upside down cake lives up to it’s name ‘for a crowd.’  A double batch of yellow sheet cake will fill up our 12×18 in baking pan giving us 20 to 30 slices of tropical cake goodness. Why the difference in serving yield? Well, if you want to keep your pineapples intact you’ll get 20 pieces of cake, but they’re pretty sizable portions so if you’re ok with cutting your pineapple slices, this cake will yield more servings.

Pineapple Upside Down Cake for a Crowd

Pineapple Upside Down Cake for a Crowd

Is there a food from your youth that just makes you feel like you’re home? Pineapple Upside Down Cake is that for me. My dad’s favorite cake, it’s the automatic go to for his birthday and every Easter. He gives up sweets for lent every. year. It warms every part of my heart to see the look on his face when this pineapple upside down cake walks in the door.

Sigh…doesn’t it feel so good to bake for other people? No really, scientists say there are scientific reasons. You should get your dose of feeling good and make this Pineapple Upside Down Cake for a Crowd, then invite over your crowd to help eat it. They will feel good, you’ll feel good, everyone’s bellies will feel good and isn’t that something the world could use a little more of?

Pineapple Upside Down Cake for a Crowd

The other really great thing about Pineapple Upside Down Cake for a Crowd? It is ridiculously low maintenance. No frosting required, just bake it all in the pan. Just don’t forget to let it cool fully before flipping the cake over to serve. Do you know what it looks like to have butter and brown sugar running all over your countertop and cabinets? YOU DON’T WANT TO, TRUST ME. I think the floor is finally loosing it’s last layer of sticky.

If preparing in advance, you can definitely refrigerate it overnight just make sure you take it out a few hours before serving so you won’t have an issue unmolding the cake. That’s it!

What’s your favorite sweet treat to make for big gatherings? Did you make this recipe? Tell me about it in the comments!

Pineapple Upside Down Cake for a Crowd

overhead view of a slice of pineapple upside down cake on a plate with a fork

Pineapple Upside Down Cake For a Crowd

Soft, light vanilla yellow cake soaked with caramelized brown sugar, butter, pineapple slices and cherries.
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Course: Dessert
Keyword: easy half sheet cakes, large cakes for a crowd, luau party cakes, pineapple upside down cake
Prep Time: 20 minutes
Cook Time: 45 minutes
Servings: 20 to 30 servings
Author: Lauren

Ingredients

  • 4 1/2 cups 570g all-purpose flour
  • 2 teaspoons baking soda
  • 1 teaspoon salt
  • 2 cups 453g unsalted butter, softened to room temperature
  • 3 1/2 cups 700g granulated sugar
  • 4 large eggs
  • 4 teaspoons pure vanilla extract
  • 1 cup 240g sour cream
  • 2 cups 480ml whole milk
  • Topping
  • 2 sticks 226g unsalted butter
  • 2 cups 400g brown sugar
  • 2 cans sliced pineapple drained
  • 1 jar marachino cherries without stems

Instructions

  • Preheat oven to 350°F.
  • Prepare the pan: melt 2 sticks of unsalted butter and pour into a 12 x 18 x 3 pan.  Spread evenly over the pan.  Sprinkle the brown sugar evenly over the butter.  Evenly distribute the sliced pineapple (5 rows of 4) in the pan with a cherry in the middle of each ring.  Set aside.
  • Prepare the cake: In a medium bowl, whisk together all purpose flour, baking soda, and salt, set aside.
  • In a standing mixer fitted with the paddle attachment or in a large bowl with a hand mixer, beat the butter on medium high speed until pale and fluffy.  Scrape down the bowl if needed and add the sugar.  Beat on medium high until incorporated, about 1 minute.
  • With the mixer on low and eggs one at a time.  Add vanilla and sour cream.  Scrape down the bowl if needed and increase speed to medium, mix for 1 minute.
  • Working in two batches with the mixer on low, add 1/2 the flour mixture followed by half the milk.  Mix until incorporated and repeat with remaining ingredients.  Scrape down bowl if needed, increase speed to medium and mix until ingredients are smooth and incorporated (about 1 minute.)
  • Pour over prepared pan, spread evenly with spatula - some of the butter may pool up around the sides, if this happens spread more cake batter in that area but don't worry too much the edged of the cake should be buttery and gooey.  Bake on the middle rack in the preheated oven for 45 minutes.  The 'top' of the cake will brown slightly during baking and edges may crisp just a touch from the butter and brown sugar, but it is all part of the deliciousness!
  • Let cool 20 to 30 minutes before serving.  To serve, turn cake over onto a large cutting board or serving platter.  If the cake is turned over before the butter and brown sugar cool and thicken, it will leak all over the countertop.

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David King

Tuesday 4th of May 2021

what can you use in substitute for sour cream

Lauren

Wednesday 5th of May 2021

Hi David - you could substitute full-fat/whole milk greek yogurt if you don't have or want sour cream.

Holly Gordon

Wednesday 26th of February 2020

I had the same issue as Beverly did, was not prepared for my kitchenaid mixer to almost spill over. The cake’s been in the oven over 60 minutes now, well-browned all over, but at 45 min. was still jiggly. I’m a nazi about oven temp (2 thermometers in there), don’t open the oven door except to check when done, and am careful about measuring ingredients. Never have this problem with baking, so not sure what I’m doing wrong. It’s for a funeral so I’m grateful for a cake that will help feed a crowd, thank you for the recipe. I’ll find out in 2 days how it came out.

For incorporating flour and milk at the end, if using a standard mixer, try mixing them in by hand a bit before turning on the mixer to prevent splashing milk and flying flour.

Lauren

Monday 2nd of March 2020

Hi Holly -

I'm sorry to hear this recipe gave you a little trouble and for your recent loss. Thank you for your feedback, I hope the end result of the cake was delicious.

Beverly Nobrega

Wednesday 28th of August 2019

Question:

I made this recipe as stated as a 1X recipe. I put in a 12X18X3 aluminum pan. At 45 min. it was still wiggly in the middle.It looks like it will be 2X as tall as your cake in the picture. Was I supposed to put this in two pans? I am serving 40 ppl. so I made the recipe twice and feel like I'm up to my elbows in cake batter. Please specify. Thanks!

Lauren

Saturday 31st of August 2019

Hi Beverly - You made it in the correct pan! It may need a few more minutes, especially if the oven was opened during the cooking process. The cake will rise the whole depth of the pan but it won't spill over.

Anne

Friday 10th of May 2019

I'm super excited to make this for my work group, but I'm worried about oven overflow because your sheet pan looks like it might be deeper than mine. It is a standard half-sheet pan that you're using that's 12x18 and about 1 inch deep?

Carol Davidson

Thursday 25th of July 2019

I want to use 5 9 x 12 cake pans as I don't have 12 x 18 cake pans, but am having trouble figuring out the amounts. Do you have it broken down into a 9 x 12 size?

Lauren

Friday 10th of May 2019

Hi Anne! Thanks for asking, unfortunately that size pan is definitely not deep enough. You want a cake pan and forgive me if I'm wrong but it sounds like you're referring to a sheet tray for baking (like cookies and what not.) The 12x18 size pan I'm using can be purchased at any craft store like Michaels, AC Moore, Hobby Lobby, etc in the cake department. It should be 3 inches deep. Hope you love this cake as much as we do!

Baker 👩‍🍳

Friday 26th of April 2019

I am making this now. 40 minutes at 350 degrees and the cake is still way undercooked. Top was getting brown , so I put foil loosely on top and the cake stuck to it! What a mess. It smells good. hope it will turn out ok since it had a lot of expensive ingredients in it, and it is for a birthday celebration tomorrow.

Lauren

Monday 29th of April 2019

The cake will brown on top while baking, but a nice golden brown. Depending on the type of pan used the baking time may vary (also preheating/whether oven has been opened, etc. can contribute to longer bake times). Per your other comment, I'm thrilled you enjoy the end result. So happy this was a delicious recipe for you!

Baker

Sunday 28th of April 2019

The cake was delicious!!! Thank you!