Double Layer Pineapple Upside Down Cake

Believe it or not, this is one gorgeous cake.

Unfortunately, the photos don’t reflect how beautiful it is. It can be hard to be a foodblogger in the Winter. I’ll let you in on a secret. I take my best photos in the daylight…usually on my porch. I have a special food photography light, but I don’t feel like I get the same kind of result. So as the day goes on, I feel like I’m racing the sunset.

I made this cake for a friend by special request, but it was evening before I could shoot it. In my opinion, the photos don’t do it justice. In person, this cake looks like a party! The pineapple and cherries glisten like colorful jewels. The white pineapple frosting and toasted pecans that surround the cake bring a beautiful textural and visual contrast.

This is a dessert with tons of TA DA!

Double Layer Pineapple Upside Down Cake
Adapted from a recipe by Paula Deen.

  • 3 cups cake flour, plus more for pan
  • 1 cup butter, softened, plus 1/2 cup, melted
  • 2 1/4 cups sugar
  • 5 large eggs
  • 1 teaspoon vanilla extract
  • 2 teaspoons baking powder
  • 1/4 teaspoon salt
  • 1 1/4 cups whole buttermilk
  • 1 1/2 cups firmly packed brown sugar
  • 2 (20-ounce) cans pineapple slices in juice, drained well (reserve 2 tablespoons juice for frosting)
  • 1 (10-ounce) jar maraschino cherries, drained well
  • Pineapple Buttercream Frosting, recipe follows
  • Chopped pecans, for garnish, optional


  • 8 ounces cream cheese
  • 4 ounces unsalted butter, room temp
  • 1 tablespoon pineapple juice from the can
  • 2 1/2 to 3 cups powdered sugar
  • Chopped toasted pecans, for garnish, optional

Preheat the oven to 350 degrees F. Spray 2 (9-inch) round cake pans with nonstick cooking spray.

In a large bowl, beat 1 cup butter at medium speed with an electric mixer until creamy. Gradually add the sugar, beating until fluffy. Add the eggs, 1 at a time, beating well after each addition. Stir in the vanilla and set aside.

In a small bowl, add the 3 cups of flour, baking powder, and salt. Stir to combine. Add the flour mixture into the egg mixture alternately with the buttermilk, beginning and ending with the flour mixture.

Divide the brown sugar evenly into each pan. Pour the melted butter equally over the brown sugar. Arrange the pineapple slices and cherries over the brown sugar. Isn’t that pretty?

You will have pineapple and cherries left over. Pour equal amounts of batter over the fruit and bake until a wooden pick inserted in center comes out clean, about 40 to 45 minutes.

Let the cakes cool in the pans for 10 minutes. Invert the cakes onto wire racks to cool completely.

To assemble the cake, carefully arrange 1 cake layer, pineapple side up, on a cake plate.

Then, I recomend that you pipe a ring of frosting around the outer top edge of the cake. The reason for this is that the cake isn’t flat on top and when you stack the second later, it will want to bend creating little cracks on the surface of the top layer of cake. The ring of frosting flattens the top of the bottom layer to receive the top later. I hope this makes sense because I failed to take a picture.

Carefully stack the remaining cake layer, pineapple side up, over the first layer (with the frosting piped around the edge). Frost the sides of the cake with Pineapple Buttercream Frosting. Press chopped pecans into sides of cake.

Slice and eat.



  1. Hi Heather, yes the photo drew me in so it does it justice! My husbands favorite cake is pineapple upside down so I know he would love me if I made this for him.

    • Suzanne you always take such lovely photos, so that makes me feel better. I always want my photos to look as good as the food does in real life and I feel like I achieve that about 25% of the time. If only photos were 3D and came with the smell o’vision. 😉 – Heather

  2. I can be empathetic about the lack of light during the winter. Your photos are gorgeous! Pineapple upside down cake is one of my husband’s favorite cakes.I’ve never considered making it into a layer cake.

  3. came across your blog while googling home made spaghetti sauce. Looks amazing and love your blog! I am following you and will be back! Thanks!

  4. What can I substitute for buttermilk? My husband is vegan (but will eat our chicken’s eggs, so that’s not a problem).

    • I believe you can substitute soymilk for the buttermilk if you also add 1 tablespoon of light vinegar (white or apple cider vinegar). The flavor will be somewhat different, but should still be yummy. You need the vinegar to substitute for the acidity that you would have gained from the buttermilk. It reacts with the baking powder to make the cake lighter. If you give it a try, let me know how it turns out. Best, Heather

      • Hi there:-). Just want to mention that we are missionaries in Mexico City, Mexico and we don’t have buttermilk available. I’ve learned to use plain yogurt in place of the buttermilk. For instance, for one cup of buttermilk, I’ll use 1/2 cup yogurt mixed with 1/2 cup milk. Hope this helps. Works for me every time:-)

        • Thans for the tip! Another thing you can do is sour regular milk with vinegar. Just substitute one tablespoon of a cup of regular milk with a tablespoon of vinegar and let it sit for 5 minutes before using. — Heather

  5. Oh my, pineapple upside down is one of my families favorite cakes. I like the double layer idea and will have to try!

  6. Heather, I just came happened upon your site today. I am hooked to say the least! I follow a few baking blogs and you are by far the sweetest – pun intended. So I feel like I won’t be punished for asking a “stupid” question… I’m not new to baking but I recently took to journaling my creations along with any photos I can manage. Sometimes I have my boyfriend shoot the pics for me because I know enough to know I know nothing about photography – especially food photography. I do understand that natural light is best as you mentioned. Unfortunately, I am an avid late-night baker and it’s not always possible for me to take photos later when daylight is available. What has always most intrigued me is the layout or setup if you will of great food photos by home cooks/bakers. I imagine these extravagent and professional looking setups people have created especially for their food photography. They look so private and uniterupted by the usual kitchen-like scenary. Whenever I lay out tablecloths or fabrics and shoot it looks pretty pathetic. My boyfriend’s camera is a nice Canon digital SLR which does a lot of the work. It pick up colors and textures of food very well. It’s just the surrounding area I seem to have so much trouble with. Are their any sites you could point me towards for newbies interested in food photography? Or any helpful hints you could provide? Most who have commented on the topic always note learning from magazines, books, other blogger’s sites, or first hand from friends/professionals. I realize it can be a lot of trial and error trying to learn what works best but I still feel pretty clueless at this point. I love to bake more than anything. Creating this journal with photos is my way of honoring what I’m doing – until one day when I might be brave enough to enter the blogger’s realm. Thanks in advance for any input you can provide!

    • Hi Kate,

      You flatter me. I feel like I still have a lot to learn. Luckily, there are many wonderful amateur and professional food photographers out there who have been kind enough to share their wisdom on their blogs. Reading about what others have done and just playing around with the camera has helped me to improve tremendously. If I were to pick out my top 3 tips, however, these would be them:

      For the background, I start with something plain, usually a plain tablecloth or even construction paper. Veggie Belly has a nice article about how to take photos on a plain white background. I’ve also used a cutting board, a white plate or the bottom of a fruit crate from my pie business. Another blogger I know found an old fence and white washed it and uses that a lot. In general, stick with natural elements and then add relevant props that seem complementary. For instance, I like to include something from the baking process (rolling pin, sprinkle of flour, chopped nuts) and/or something fresh and colorful. For instance, I like to include fresh apples in the shot of my apple pie or fresh basil on top of or near a bowl of pasta that features basil.

      Another tip that I use all the time is to shoot the food from an unusual angle. I often take the shot from the side or maybe from directly above to get a different perspective.

      Just as important as the setup, however, is the amount and quality of your light. It took me a few months to figure this out and I’m still learning about it. I take my best shots outside on an overcast day, my second best on my covered porch on a sunny day. In general, I seek out natural indirect light. Surprisingly (surprising to me anyway), food doesn’t look good in direct bright sunlight, but can look awesome in the shade with the right light balance. Don’t be afraid to setup the scene outside like it is inside. Nobody will know.

      Since you do a lot of night photography, I definitely recommend getting a broad spectrum florescent light. Regular camera flash makes food look unappetizing. I use the Lowel EGO Light. Steamy Kitchen has a nice take on how the light improves photography. I only have one Lowel EGO light, but I could really use two because shadows can be an issue at night. Sometimes I even use the light during the day in combination with natural light depending on how bright it is outside. Also, I shoot in RAW to ensure that I can play with the white balance later. If the photo is too blue or too green, again, unappetizing.

      I take TONS of pics and only select the very best ones for the shot. I edit those using Adobe Photoshop Elements and Iphoto. Mostly I lighten photos, change the white balance and take out the occasional blemish. Some bloggers edit much more, completely changing the feel of the picture. I simply don’t have the time or software. But if you do, Adobe Lightroom is supposed to rock for photo editing.

      That’s the bulk of it. Good luck and just try it out. You will learn a lot by doing and if you don’t like it, the delete button is just a click away.


  7. This was a good cake. The frosting took me by surprise, as I’ve never had Pineapple Upside Down Cake with frosting. It was a tad too sweet, but I still used it. The presentation was beautiful. Great work. Love the photo.

  8. If I wanted to make this in 10 by 2 rounds, how would you suggest I adapt the recipe as far as adding more cake batter?

    • I would probably recommend that keep the same amount of batter and make the case slightly less tall. You may be able to reduce the cooking time a bit to compensate. However, if you don’t want to do that, you could increase everything by about 25% and keep it the same height. Let me know how it turns out. 🙂 – Heather

      • Thanks for your quick response, the reason I asked is because my husband and I are making 2 cakes to serve 40 people. One of them will be your lovely recipe. I just wanted to make sure we had enough cake, which is the reason we selected the 10 X 2 pans. I will let you know what we do! Again, thank you.

  9. Love the picture and I just put my two pans in the oven!!! So excited to taste this cake, I’m not that much of a sweet tooth, but my husband on the other hand is!! And my mother in law is a baker and so he grew up eating the best of the best sweets lol I am guilty of not baking for him as much as I should here and there, and know that tonight for dinner he will be surprised when I take this yummy cake out to serve yay he will be happy!! Thanks for the yummy recipe.

    • I am baking this cake tomorrow. How did your cake turn out. I know it was delicious.

      • I didn’t get to eat it, but reports were positive. 🙂

      • My cake turned out wonderfully! I did not get to taste it unfortunately, it was for a party we catered. However, my friend who did taste it said it was delicious! Thanks for the recipe. We used 2 10X2 round pans and used one recipe plus one half of the recipe. I made sure to use a measuring cup to put equal amounts of batter into each pan. The cake was pretty large but perfect for the amount of guest. Thanks again.

  10. I am making this cake for my soon to be father in law. Can I add rum to this? If so, what would the measurements be? Thanks 🙂

    • Hi Ann Marie,
      I suppose you could add a couple of tablespoons of rum to the butter/brown sugar mixture you place at the bottom of the pan before you add the pineapple. And/or you could substitute rum for all or part of the pineapple juice used to flavor the frosting. Mmmm. That sounds good. Let me know how it turns out. – H

  11. How many people should this be suitable for?

    • A lot. It is pretty big. Paula’s original recipe says that it serves 8, but those would be meal-sized servings. I would say you could feed 12-14 people with this cake depending on the size of the slices. – H

  12. I made an upside down pineapple cake for my girlfriend….when it came out the oven, it was soooo flat. I guess I used too large of a pan. So I googled cakes and when I came across yours, it stopped me in my tracks! How awesome! I gave mine to the family and have YOURS in the oven. I hope it comes out as good as yours looks. I did get “Bowl-licking” approval! HA HA! Thanks for sharing this awesome recipe.

  13. Heather S,
    If I wanted to make this in cast iron skillets, do I need to make any adjustments to the cooking time?

    • Hi Eddie,
      I would think that cast iron would get too hot to make this well, possibly burning the sugar/fruit on the bottom/top, but I’m really not sure. If you try it, let me know how it turns out. – Heather

      • Heather S,
        It turned out wonderful and delicious. I made it in 2 cast iron skillets and used the same cooking time. I also added some rum to the pineapples and brown sugar in the bottom of the pan. The cakes came out with a nice dark brown glaze, with a caramelized rum flavor in the pineapples. It was a huge hit with the family.
        Eddie C

  14. I am wanting to make a three tier pineapple upside down cake for a wedding, my first question was had anyone tried making this in square pans, I have a 6-8-10 I’m going to use,,, also does anyone know how to make this for diabetics guests as well!! I’m making two cakes on, the regular cake u have listed above just square, and another that is diabetic friendly…thank you for any replies anyone!!??

  15. LOVE pineapple upside down cake but have never served it with a cream cheese frosting. Must try it. But I always use this frosting (laced with orange zest) on my carrot cake. However, that much icing sugar is way too sweet for my taste. No problem cutting down, doesn’t adversely affect the texture of the frosting at all.

  16. Does the cake need to be refrigerated once it is baked ?

    • Nope.

  17. Yup! You should always read a recipe through before attempting. I didn’t get to the part about the ring of frosting in the middle and guess what??? Splitsville. But, it tasted great.


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