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Pineapple Upside Down Cake

I have been tasked with making this for my cousin's surprise birthday party in a couple of weeks. Her late mother made "the best," but alas I never tried it. From what I understand, a cast iron skillet and fresh pineapple are a must. I need some tips and recipes so I can start practicing. I don't even know if it is served warm, with ice cream, can you make ahead? Help!

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  1. Have you searched here? It is easier to make with canned slices than fresh.

    1. Silver Palate has an excellent Pineapple Upside Down Cake. It uses canned p'apple and pecans. I couldn't find it on their website.

      1 Reply
      1. I agree with using cast iron. I use canned pineapple rings...and real butter.

        1. Grease the pan so it comes out easy. Serve warm or room temp with soft whipped cream.

          Once you get it down, you can experiment with different versions, like gingerbread pumpkin upside down cake topped with apple slices and cranberries, or the one I'm trying soon topped with bananas,rum and nuts. Good for breakfast parties too.

          1 Reply
          1. re: coll

            It is also really good served cold, but I understand this is not the traditional way outside of Southern, IN. Leftovers should definitely be put in the fridge and enjoyed cold though. I think I'll be making pineapple upside down cupcakes today.

          2. http://www.epicurious.com/recipes/foo...

            I think this may be just what you are looking for! Good luck!

            1 Reply
            1. re: Tehama

              Tried this recipe last night as my first attempt. I opted against recipes with cake mix, cherries, canned pineapple or nuts, so this one appealed to me. The dark rum also seems like a key ingredient.

              I followed this recipe almost to the letter, except for cardamon I substituted 1/2 tsp cinnamon and 1/4 tsp cloves. I think I would start checking for doneness at 35 minutes next time. It didn't overcook - but got pretty dark on top (bottom?) after 45 minutes.

              Success! We almost devoured half the cake last night. How could I have lived 30+ years and never tried this cake?! Brought the rest into the office today and received good reports from all. I think I will still try 1-2 more recipes, but this one is definitely a contender. Thanks!

            2. I just checked in at the TasteSpotting site and this is the first thing up. Looks really good except no cherrys.


              1. Wow - thanks everyone for all the tips and links. I had searched on this site, but since I can't seem to figure how to just search one board, I get lots of results for eating - rather than baking - PUDC. The long name probably doesn't help either.

                Will be buying fresh pineapple today!

                  1. Pineapple Upside-Down Cake


                    1/2-cup butter (1-cube, 1/4-lb)
                    1-1/2 cups brown sugar
                    1 (20 ounce) can sliced pineapple rings - reserve liquid
                    7 to 10 maraschino cherries - without stems

                    1 (18.25 ounce) package yellow cake mix
                    3 eggs
                    1-1/3 cups water / pineapple juice from above can
                    1/3 cup cooking oil


                    Preheat oven to 350 F.

                    In an 11-inch cast iron skillet on the stove-top, over medium high heat, melt 1/4-pound of butter. Remove from heat.

                    Sprinkle 1-1/2 cups of brown sugar evenly to cover melted butter. If needed, even out layer of brown sugar with a fork.

                    Arrange pineapple rings around the bottom of the skillet, on top of the brown sugar, one layer deep. You will probably end up with six pineapple rings around the edge of the skillet and one in the middle.

                    Reserve pineapple juice from can.

                    Place a maraschino cherry in the center hole of each pineapple ring.

                    In a 2-cup measuring cup, mix pineapple juice from can with enough cold water to make 1-1/3-cups of liquid.

                    In a large mixing bowl, mix at low speed until moistened, 1 (18.25-oz) box of yellow cake mix, 3 eggs, 1-1/3 cups of water/pineapple juice and 1/3-cup of cooking oil.

                    When cake mix ingredients are moistened, mix on medium speed for 2-minutes.

                    Pour the yellow cake mix batter over the pineapple/cherry layer in skillet.

                    Place skillet in oven, on center rack, and bake for 45-55-minutes or until a cake tester inserted in the center of cake comes out clean.

                    Remove from oven, place a plate over skillet and carefully turn cake out onto the plate immediately. If you wait until later to turn out cake, the brown sugar layer will stick in the skillet.

                    6 Replies
                    1. re: Antilope

                      You're right, you have to use boxed cake mix to make it authentic.

                      1. re: coll

                        If you're going the boxed route, I bet a pineapple cake mix would be good as well.

                        1. re: ArikaDawn

                          They make that? (I've been making from scratch myself though, just thinking of my Mom)

                          1. re: coll

                            Yea, I just saw it for the first time a few weeks ago, but my mom said it has been around forever. She makes a cake every year at Easter that is soooo good and I always assumed it was from scratch, but apparently one of the layers is the pineapple cake mix. Still good.

                            1. re: ArikaDawn

                              But Antilope has the right skanay on it by using the juice from the can to flavor the cake mix. Works if you use pound cake mix, too.

                              1. re: yayadave

                                Yeah that's what my mother always did, it was her big "secret", that's what made me say it was "authentic".

                    2. I made one a few months ago (used fresh pineapple), and my big learning from that was to put the cast iron skillet over a baking sheet since there were lots of juices that bubbled up and left a big mess in the floor of my oven.

                      The upside down cake was fabulous though!

                      1. I made one with an almond pound cake recipe I found and soaked the pineapple in a brandy, brown sugar, buttery glaze. I served it slightly warm with vanilla bean ice cream and extra brandy glaze drizzled on top. The cake was gone in 2 seconds! Seriously. Whatever you do, I would definitely serve it warm i think that's the key.
                        Have fun :)

                        1. I learned the hard way not to try to make one in a springform pan.

                          1. Martha Stewart has a great one on her website. Its from Everyday Food. Its called LIghter Pineapple Upside Down Cake. It uses fresh pineapple and buttermilk. I got rave reviews when I made it.