Pineapple Upside Down Cake

It’s dessert day here in camp, and y’all are in for a good one today … our version of the classic Pineapple Upside Down Cake. This homemade gem is even more impressive when baked in a Dutch oven.

Cooking cakes in a Dutch oven can be a little tricky, because you are dealing with some moisture, and you could have to deal with some wind when cooking outdoors. But this one’s got that extra little hard factor–a lot of brown sugar on the bottom with some butter. You get that caramelized effect but also it can burn quicker. So we’re going to show you how to manage this today and make you  the star of the neighborhood and the campgrounds.

Let’s Get The Pineapple Cake Going

We have got a 10-inch Dutch oven, where we’ve melted 1/2 stick of butter. To that, we’re going add 1/2 cup of brown sugar; just sprinkle it around, mash it with a rubber spatula and incorporate it into that butter. Put canned pineapple slices on top of that sugar/butter mixture making sure to cover the bottom of the oven. Save the pineapple juice, because we’re going to use it later.

For a little color and extra flavor, get some maraschino cherries, sprinkle them lightly with a little almond extract then use them to fill the holes of the pineapple slices.

Almond extract enhances the the flavor of both pineapple and cherries.


Mixing the Dry Ingredients and Batter Separately

Mix your dry ingredients in a separate bowl. We’re going to use 1 1/2 cups of flour and to that, we’re going to add about a teaspoon of salt. A couple of teaspoons of baking powder. Mix the dry ingredients well and set aside.

Now, it’s time to work on the batter. Start with 1/3 cup of shortening. Next go ⅔ of a cup of sugar. At this point, mash the shortening and sugar together, then add one egg, a teaspoon of vanilla and mix well until all the lumps are gone. Add 2/3 cup of milk and mix it lightly before adding the flour mixture to it.

Gently add the flour mixture to the batter. Fold it around incorporated it into the batter, a little at a time, being careful not to over stir.

Pour the batter into the Dutch oven and spread it evenly over the pineapples. We find it’s easy to put it down in dollops and then spread with a spatula, making sure everything is covered.

Time to Cook the Pineapple Upside Down Cake

When cooking our Pineapple Upside Down Cake over the fire, we put it on a tall trivet. The reason is this cake needs to cook slowly and the tall trivet is one way that we can regulate heat. We’re not putting it on something short or setting it directly in the coals. Put a good, light circle of coals a pretty good distance from that Dutch oven. That will give us the slow start we’re looking for. If we need to speed things up, we can push the coals closer. There should never any coal directly underneath, unless we need to target some heat right at the end.

The top is covered pretty lightly, as well. If the wind is brisk, you’ll need to rotate to even out the hot spots. Rotate the top one way, the bottom the other way. You want to cook this cake as slowly as you can, especially with all that brown sugar and butter on the bottom.

If you don’t have a trivet, it can still be done. Just make sure that you have even a lighter ring of coals at a pretty good distance from your Dutch oven. Remember, heat will travel, especially on a windy day.

We need to cook this cake slowly, so you will want to maintain the heat.

If you notice that it’s hotter on one side or another, pull those coals a little farther back. Unlike other cakes, there is no cake batter on the bottom. So, we’re caramelizing the juices on the bottom while cooking the batter on top. You’ll see the juice bubbling up around the batter. Check it occasionally to see that it’s browning evenly on all sides or if you need to pull the coals away even more.

With other cakes you may sometimes need to target the heat, or slow it down. With Pineapple Upside Down Cake,  everything is right on top, so just wait for it the batter to brown, get firm and set up. If you think it’s cooking too fast, you can set it off the fire.

The Deal is Done!

When the cake is a nice, even brown color, get a toothpick and insert it into the cake. If it comes out dry, your cake is ready. Run a knife along on the edge of the cake to make sure that it is loosened from cast iron.

Use that same toothpick and poke a few holes around the top of the cake. Remember that juice from the pineapple we saved? Mix that with any cherry juice that may have been left over and pour over the top of the cake, letting it seep into the holes.

Get a plate that fits the size of that Dutch oven (the closer to the cake, the better), flip the Dutch oven over and let it set for a few minutes. That way, when you flip the oven over, the cake and all the gooey goodness will come out easier.

Remember, the closer your plate is to the cake, the less chance of the edges breaking when you flip it over and out.

Check out our video below to see how to cook our Pineapple Upside Down Cake in your Dutch oven. Please share the recipe and the cake with all your friends and neighbors, and enjoy!

Pineapple Upside Down Cake - Cowboy Kent Rollins


  • 4 tablespoons butter melted
  • 1/2 cup light brown sugar packed
  • 1 15 ounce can pineapple slices in juice reserve the juice
  • 7 maraschino cherries reserve the juice
  • 1 teaspoon almond extract
  • 1 1/2 cups sifted all-purpose flour
  • 2 teaspoons baking powder
  • 1/2 teaspoon salt
  • 1/3 cup Crisco
  • 2/3 cup sugar
  • 1 large egg
  • 1 teaspoon vanilla extract
  • 2/3 cup milk


  • Add the butter to a 10 inch dutch or cake pan and swirl around to evenly coat the bottom. Grease the walls with additional butter or cooking spray. Sprinkle the brown sugar in the bottom of the Dutch oven or pan and lightly mash around with a spatula to create a crust. 
  • Place the pineapple rings in an even layer on top of the brown sugar.
  • In a small mixing bowl combine the cherries and almond extract. Place the cherries in the center holes of the pineapples.
  • In a medium bowl, combine the flour, baking powder, and salt.
  • In a large bowl, lightly stir together the Crisco and sugar. Whisk in the egg and vanilla until smooth. Whisk in the milk.
  • Slowly stir the flour mixture into the milk mixture and fold in with a spoon. Be careful not to over stir. Spread the cake batter evenly on top of the pineapples.
  • Bake in a preheated oven at 350 degree F for about 40 minutes or until an inserted toothpick comes out clean.
  • Meanwhile, in a small bowl combine 1 ½ tablespoons of the leftover pineapple juice and 1 ½ tablespoons of the cherry juice. When the cake is done baking, poke several holes in the cake and pour the pineapple juice mixture evenly on top. Let the cake rest for 2 to 3 minutes.
  • Score the outside edge of the cake and place a plate over the cake and invert. Let the cake rest for about 5 minutes to let the juices run down from the bottom of the Dutch oven or pan before removing. Remove and serve.
Tried this recipe?Let us know how it was!