Pineapple Upside Down (cup)Cake

FullSizeRender (14)I must confess…I have not been immune to the cupcake craze. I wish I was, or rather my waistline does. It’s just that they are so tiny and yummy.

I have experimented with lots of varieties. Today’s post highlights one of my favorites….the pineapple upside down cake. Oh. My. Gosh. I generally have a rule that fruit cannot be dessert. I mean really, can something without chocolate be dessert? Normally my answer to that question is a resounding NO. But this little cake has wormed its way into my heart….and my list of official desserts.

So, without further ado….here is what you’ll need


1 Box Duncan Hines Pineapple Supreme Cake (Yes…I know this is a box cake. SHHH!)

4 eggs

3.4 ounce package of instant vanilla pudding

1/2 cup oil

1  cup water

1 1/2 Cup butter, melted

about 1/2 cup brown sugar

Pineapple slices


1 1/2 sticks butter, softened

1 tsp vanilla extract

1-2 cups powdered sugar (depending on how sweet you like it)

1/4 cup (or so) of heavy whipping cream

1/2 cup crushed pineapple

cherries to garnish if you want

In a mixer, blend the cake mix, pudding, water, oil, and eggs. Mix on slow until the ingredients are incorporated. Turn up mixer and beat for about two minutes.

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In your cupcake pan, put a spoonful of butter into each cupcake hole.

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Spoon some brown sugar on top of the butter.

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Cut up your pineapple slices and place a few on top of the butter/sugar mixture.


Scoop your cake mix on top of the pineapples. Fill about 3/4 of the way full and bake for 18-22 minutes on 350 degrees. I know they are ready when I can touch the top and it springs back.

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Ok, so this is an important step. I didn’t do it the first time I made them and I ended up with a mess! As soon as these little babies come out of the oven, use a butter knife or a spreader to run around the edges of each cake.

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Do NOT let these cool! You have bubbly delicious sugar in the bottom and it will harden fast. I let mine sit for 2 minutes before I turn them. I use my cooling rack. I place it on top of the cakes, grab some pot holders and make sure I have a good old on both the pan and the rack. BE CAREFUL HERE!!!I

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Flip the pan and tap the top of each spot. Let gravity do it’s thing for about a minute, then lift the pan.

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Look at these yummy little things….

Let them cool while you go make some amazing pineapple buttercream icing.

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Put your softened butter and vanilla in the mixer and let it go! I beat the butter for a bout a minute to get it really good and soft. Then add about 1 cup of powdered sugar.

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Then, add the crushed pineapple and blend for about another minute or so. (Drain as much of the juice as possible from the pineapple before you add it!!!)

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Add the heavy cream and mix on medium-high for a good solid minute or two.

(Ok…let’s stop here for a second and explain. This my fellow baker is my newest addition to icing. I realize I should have figured it out by the name butter-cream, but I guess I’m a little slow. It simply took an episode of Cupcake Wars to realize THIS is the solution to overly sweet icing. It will make your icing light, fluffy and the perfect amount of sweetness.)

Now….at this point you need to taste your icing to see what needs to be added. If it is too thin, add a little powdered sugar at a time until it thickens up. If you ever make it too thick, add a half a teaspoon of cream at a time until it is a good consistency.

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I use piping tip 12 for this cupcake. This is simply a big hole. I tried using a tip that would make a prettier finish, but the pineapple kept getting stuck. If that happens, just unscrew the tip and clean it out. This tip gave me no problems!

I always refrigerate these after I ice them. It lets the icing harden just a little bit. If you want to place a cherry on top, go for it. I just can’t make myself like them. (It reminds me too much of medicine…yuck!)

ENJOY!!!!! 🙂

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