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Pineapple Upside Down Cupcakes

Pineapple upside down cake is a sinfully southern dessert and one that I've never made....until now.  Well, I made a mini version.  When I saw these sweet little individual cakes here, I was sold.

Baby steps.  

Next on my list is making an entire cake southern style in my cast iron skillet! 

These pineapple upside down cupcakes were really easy and the trickiest part was sizing the canned rings to fit my muffin tin.  If you own a jumbo muffin tin, that would be ideal but here's how I made it work.

Just cut a small portion out of the ring and squeeze together to fit your tin!  Leftover pieces are free for snacking. 

Here's what you'll need to make this happen.  And trust me, you want this to happen.  This recipe easily made 8 portions.


2 eggs
2/3 C white sugar
4 T pineapple juice
2/3 C all purpose flour
1 tsp baking powder
1/4 tsp salt


1/2 stick butter
2/3 C brown sugar
2-cans pineapple rings
8-maraschino cherries

Preheat oven to 350 degrees.  Spray your muffin tins with non-stick cooking spray.  

In a mixing bowl, add eggs, white sugar, and pineapple juice.  Beat for 2 minutes.  In a separate bowl, sift together the flour, baking powder, and salt.  Add to the wet ingredients and turn mixer back on for 2 minutes. 

In a small sauce pan, melt the butter and add the brown sugar.  Stir on low heat for one minute.

Place a pineapple ring in the bottom of each jumbo muffin tin.  Add a cherry in the middle of each pineapple.  Spoon over a layer of the warm brown sugar mixture.  Pour cake mixture over to fill muffin tin 3/4 of the way full.  

Bake jumbo cakes for 25 minutes.  Bake regular cakes for 20 minutes. 

Cool the cakes for about 5 minutes then gently run a knife around the edges to loosen the cakes from the pan.  Place a wire cooling rack on top of the muffin tin and flip over to release the cakes onto the wire rack to continue cooling.  You may want to place another cookie sheet underneath the rack as they cool because they will drip a lot.  Oooey Gooey goodness!


  1. This has got to be a sign. I keep telling myself to make mini pineapple upside down cakes because hubby looooves it. Yours look amazing! Have a great weekend, darling!

  2. yummy, love pineapple upside down cake, it was something my mom made for me as a kid and now my hubby makes it for me. I have a fear of the

  3. You never mentioned how long to cook them for! I'm trying your recipe tonight, so I'm going to wing it :)

  4. Snarky Sweets,

    You are so right! I apologize for leaving you hanging. I've updated the recipe with further cooking instructions and cooling details.

    I hope your cakes turn out great! Enjoy.