Upside Down Pineapple Muffins
- Tracy Scheckel
- 2 days ago
- 5 min read

This was one of those rabbit hole days for sure. I store all my photos in the cloud and every day I get a notification to look at my photos for today over the years. Recently, I saw photos from when I shared my pineapple upside down cake recipe and associated mommy trauma. THAT, gave me the crave to make a cake.

Then, because I recently purchased those cool silicone muffin cups, I thought, I wonder if I can make individual cakes (muffins)? I did some Googling to see what others had done and set to the task at hand. My biggest concern was getting the perfectly caramelized pineapples slice in each muffin. I came close, but because I was a bit hasty with the frozen cherries I decided to use in place of Maraschinos, I messed it up. N Ext time, I'll thaw them completely, drain them and dry them a bit. And there will be a next time, these ware delish and beautiful to plate.
For 12 pineapple upside down muffins, you'll need two 20oz. cans of pineapples in pineapple juice. You'll have extra slices, but they won't go to waste. You'll want to drain those pineapples and reserve the juice. While you can use the jarred cherries, I like the Wyman's frozen cherries; there are 3 varieties in on freezer bag. Thaw, drain and dry a dozen of them for the center of your pineapple slices (I like random varieties, but you can certainly pick out whichever you prefer if you have a preference).
I did 2 things to help encourage the caramelization: first, I set the silicon muffin cups on a cast iron griddle when it was time to bake, and second, I melted the butter and brown sugar in a saucepan and boiled the mixture for a few minutes. What I would have done differently was to eliminate as much cherry liquid as possible AND preheat the griddle while the oven was heating.
I used a boxed cake mix, but when I was researching, I noticed that some folks increased the amount of eggs from the one or two that the box recommends to 3. AS I do with my regular recipe I use pineapple juice in place of the water that's called for. While the caramel was 'cooking' I brushed each cup with some vegetable oil to help avoid any sticking.
With a small ladle, I divided the caramel mixture evenly between the cups. Since the pineapple slices were a tad big, I slit them to allow me to coil them a bit so they would fit into the muffin cups. After the cherries were placed I filled each cur a bit more than 2/4 of the way.
After they baked for 25 minutes or so, I let them cool a bit and attempted to invert one (on the right in the center image. It was not very caramelized and dribbled most of it's liquid onto the pan. The one on the left was sitting on the cast iron for another half hour and appears to have caramelized further just sitting on the counter out of the oven, but on the hot pan. This is what led me to think about preheating the pan next time. Ultimately, I refrigerated them until a half hour before serving. To plate them I mixed up some whipped cream with brown sugar and swirled it on the individual plates, inverted the up in the center, swirled any juice that drizzled and dropped a couple of frozen raspberries around as a garnish.
Also, along with the leftover pineapple slices I mentioned was some cake batter -- so another experiment..... I melted a bit more butter and brown sugar and after placing a piece of parchment paper in a shallow layer cake pan, placed the pineapples, poured the caramel, and used some frozen raspberries in place of cherries, before pouring the batter on top.
I baked it for 15 or so minutes and after it cooled a bit, attempted to invert it. It wasn't pretty, but it was delicious and I am decidedly planning to eliminate cherries for raspberries for all future pineapple upside down recipes. What I'll do differently next time is use a deeper pan, pour the caramel in before the pineapple layer. My thinking is that this really thin 'pancake' -- assuming I can get it out of the pan looking pretty would be a lovely addition to a 'second breakfast'. New term folk -- second breakfast -- according to my friend Steve is a breakfast where you add some sweets. I asked if that wasn't actually brunch and he informed me that brunch introduces liquor. Learn sumthin' new every day..... Anyway, once this is perfected, I'll issue an update. For now, I'll get to the actual recipe for the muffins.
THE RECIPE:
2 cans {20 oz. each} of pineapple slices in pineapple juice drained with the juice reserved and separated
For the caramel
1 C dark brown sugar
1 stick of butter
1/4 C pineapple juice
For the cakes
vegetable oil for prepping the cups
1 boxed yellow cake mix
1/3 C vegetable oil
3 eggs
1 C of the pineapple juice
12 cherries (or raspberries)
For Plating
1 C whipping cream
1/4- 1/2 C brown sugar
Berries (optional)
While the pineapple is draining, heat 1 stick of butter in a sauce pan, add the cup of dark brown sugar and 1/4 cup of the pineapple juice.
Bring the caramel to a boil and simmer for 5 to 7 minutes stirring very often and keeping an eye that it doesn't boil over or burn.
Brush the inside of the muffin cups with vegetable oil and preheat the oven to 350 degrees.
Learning from my first time out, place a cast iron griddle into the oven to preheat. (If you don't have a griddle or a piece of stoneware, juts prep the cups on a rimmed baking sheet.
To ix the cake, combine the boxed mix, 1/3 cup of vegetable oil (or melted butter if you really want an artery killer), and the full cup of pineapple juice and blend until it's smooth.
After removing from heat and letting it set a minute or two, using spoon or small ladle divide the caramel evenly into the muffin cups
Fit a pineapple slice into each cup
Place a drained, dried cherry into the center.
Ladle cake batter to 1/8" inch of the top of each cup.
If you preheat a griddle or stone, be very careful placing the cups on the hot surface.
A flap pancake turner slid under the cups with your other hand to steady will make it easier to make the transfer.
Bake for 20 to 25 minutes until a toothpick comes out clean.
Remove from the oven and let them sit on the basking pan until cooled to room temperature.
Refrigerate until a half hour before you're ready to serve them.
If you're into the presentation, you can combine the whipping cream and brown sugar and whip until peaks form.

Place a mound of the brown sugar cream in the center of a dessert plate and swirl it out a bit with a spoon.
Invert the muffin cup in the center of the plate on top of the cream and remove the cup by gently pressing down on the bottom center and lifting straight up.
If any of the wonderful caramel oozes, give it a little swirl onto the cream with that spoon.
Drop a few berries for garnish.

































