Pineapple Upside Down Cupcakes

A while back, I posted pictures of a dozen jumbo pineapple upside-down cupcakes that I made for a birthday party. I received quite a few personal inquiries as to the recipe and technique so I have decided to post it here.

I must warn you: these are not vegan by any means. I suppose I can make them vegan quite easily but I have not tried to yet, so I’m just going to post the recipe as I have received it. Where necessary, I will print suitable substitutions for the eggs and dairy.

I have served these numerous times for friends and family members and I must say, I get the best reviews from them. They are so moist and with such a tender crumb, the pineapple so sweet and juicy, I can’t imagine a better treat to serve to the people you love. There are accompanying pictures to help you through the process.

Please enjoy and feel free to email me with questions! To start, you will need:

wax paper, cut into large enough squares to cover most of muffin cup, but not necessarily all

6 Tbsp butter, divided (I’m sure you could vegan margarine here)

1 cup packed brown sugar

2 Tbsp light corn syrup

1 large can crushed pineapple, well drained

12 maraschino cherries, well drained

3 eggs (you can probably use flax eggs here, or if you want a little more tropical flavor, try bananas. I don’t know if I’d try tofu, though)

2 cups sugar

1 cup canola oil

1 cup sour cream (vegan sour cream would be fine here)

2 tsp vanilla

2 1/2 cups AP flour

1/2 tsp baking soda

1/2 tsp baking powder

1/2 tsp salt

Line your regular sized muffin tins with the wax paper, then spray the paper with no-stick. Don’t skip this part. It’s a sticky enough mess at the end without extra gunk to scrape so just do it. In a small saucepan, melt the butter over low heat; stir in brown sugar and corn syrup. Cook over medium heat until the sugar is mostly dissolved. Remove from heat, spoon a bit into each muffin cup; top with pineapple bits and a cherry. This is what it will look like:

In a large mixing bowl, beat eggs and sugar until thick and lemon colored. Beat in the oil, sour cream, and vanilla until smooth. In a separate bowl, combine flour, baking soda, baking powder and salt. Add to egg mixture, mix well.

Fill muffin cups two-thirds to three-fourths full. Bake in a 350 degree oven for 25 minutes or until the tops have golden brown edges. Let cool in the pan for ten to fifteen minutes. You want the brown sugar mixture on the bottom to not be a runny liquid anymore. It should be somewhat thickened.

Next, you are going to take them out of the pan, flip them over, and let them cool completely. There might be a drip or two down the sides of the cupcakes so you might want to put them on wax paper for easier clean up. They will look like this:

Once they are cooled completely, it’s time to take the wax liners off them. Be careful! There is no way to get them off without pulling of a tiny bit of cake here or there but they still look amazing and taste even better so try not to worry about it too much.

Start from the bottom of the wax paper and pull all the way around before pulling the top where the pineapple is. This is why you need to spray the papers with no stick spray. It’s going to look like this:

Once you have done this, take a knife and gently scrape down the pineapple tidbits and spread them on top of the cupcake where they belong, like this:

It is a little tedious but I promise that when you see people’s eyes roll back into their heads…it’ll be totally worth it. You should have a bunch of papers that look like this:

See how they all have a few crumbs of cake on them? It’s unavoidable, really. But the end result will look l ike this:

When I first received this recipe, it stated to use a fresh, whole pineapple cut into rings, but I decided to make the original recipe for only twelve treats stretch a little further by making them twenty-four regular sized muffins. Rings will only work if you want to make jumbos, which I have done before, and they were amazing, of course. There’s no real need to drain the fresh pineapple as much as the canned, either. You can use canned rings if you don’t want the hassle of cutting up the awkward, spiny fruit but still want to make these jumbos.

I’m going to try this week to completely veganize this recipe and I will repost with my results. Good luck and I hope you enjoy these as much as my family does!

Ps- if you are seeing pictures that look like they aren’t supposed to be here, please let me know. While uploading pictures to this post, I have the right ones, but when I make the post public, it keeps showing me pictures that I didn’t put up. Weird. And irritating.


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2 responses to “Pineapple Upside Down Cupcakes

  1. Pammy

    Hi, Im curious you baked wax paper? When Ive baked it , it starts to smoke in my oven. Can you use parchment.

    Please let me know,

  2. geist

    Parchment would need to be put in the cups, not waxed paper. But, I would just use non-stick pans and spray with Pam (or similar). The parchment isn’t even necessary (without it, you don’t get the peeling and crumbs!).

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