Have you ever been flipping through a magazine in the checkout line and notice a dessert called “Pineapple upside down cake,” but it looks perfectly right side up? It’s an interesting concept, but the topping is cooked on the bottom and then flipped! I have to thank King Arthur Flour for the base of this recipe! Either way you slice it, this is a delicious cake! Here’s how:


Cake batter:


2 C All-purpose Flour

2 t baking powder

½ t salt

½ t ground cinnamon (if you’re more of a cinnamon guru, up this to ¾ t)


½ C butter (1 stick) unsalted butter, room temp

1 C granulated sugar

2 large eggs, separated, room temp

½ C milk, room temp

1 t vanilla extract


2 tablespoons of butter, melted

½ C Dark Brown Sugar

½ C Light Brown sugar

20 oz can pineapple rings preserved in pineapple juice, drained

24 maraschino cherries (you can get by with 15 or so. . . )


Other Stuff:

Large mixing bowl

Stand mixer/hand held mixer fitted with paddle or beaters

High sided small bowl for beating egg whites

9” (measured of bottom diameter) X 2” cast-iron skillet. 

Pastry brush/silicone basting brush

Serving platter at least 11”in diameter.



Separate Eggs and allow to come to room temp along with butter. Drain a 20 oz can or pinneapple rings.  (I generally set out my eggs to come to room temp then separate. . . whatever works best for your time frame. . . )

Preheat oven to 350 DegF with racks placed in the middle and lower third of the oven. 

Whisk together the Dry ingredients in large mixing bowl and set aside.

Break up the butter until it coats the bowl and then add sugar and beat/cream for about 3 minutes. Meanwhile, with a whisk beat your egg whites until frothy and set aside.  

Make sure to scrape down the sides of the butter bowl at least once during the creaming process. Add the egg yolks to the butter and sugar and mix and scrape the bowl once more. Add in vanilla and whiz once more.

Now you’re ready to mix in the Dry ingredients alternating with the milk, starting with 1/3 of the dry, ½ milk, 1/3 dry, ½ milk and ending with the last third of the dry. The batter will be rather thick here.

It’s now time to fold in the egg whites. Slack the batter up with 1/3-1/2 of the egg white mixture by “cutting down the middle and going round the outside.” Continue until no frothy white mixture is visible. Fold in the last of the egg whites.  After your batter is smooth, set it aside while you prepare the pan and topping.

In your skillet, melt the butter make sure to work it around the pan bottom and pull it up the sides of the pan with a pastry/basting brush to ensure the release of the cake batter once baked. Sprinkle and spread the brown sugar mixture over the bottom of the pan atop the butter. Don’t “pack” it.  Cover with drained pineapple rings. The size of ring/pan will determine the actual number, but mine is generally between 7 and 8. . .  Pour over rested batter and spread evenly across the pineapple and brown sugar topping.

Place in the middle of the oven for 40-50 minutes.  I like to turn my pan ½ way through a la “20 and turn.”  Mine took about 42 minutes total to bake. The cake is fully baked when it’s a nice golden color, it bounces back, and a cake tester comes out clean. 

After baked, within 3 minutes, loosen the sides of the cake with an offset spatula or butter knife. Then place your serving platter on top of the pan and invert the cake. If one or two of the pineapples have stuck, DON’T worry! You can scrape them off and make sure to put the brown sugar side up on top of the upside-down cake.

THEN, put on your cherries in the middle of each ring and in any space that you see fit. I try to make mine as symmetrical as possible. 

NOW, you need to let the cake cool for about 30 minutes before serving. The BEST part is this cake will last for several days in the fridge wrapped directly with plastic wrap. SO, you could even make it a couple of days ahead during a busy holiday season!

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