Easy Pineapple Upside-down Cupcakes are a foolproof way to enjoy a classic dessert! These mini cakes are perfectly proportional and won’t take you long to bake!
Let me start by saying that any recipe that requires me to “flip and pray” is not usually my forte. But pineapple upside-down cake is my dad’s favorite so I guess I had to give it a try. That’s why I decided to make the mini version – there’s a lot less risk involved.
Although it’s a fruity dessert, it is still so rich and buttery – I can see why my dad loves it. This recipe is made with a standard box cake mix, only taken to the next level with brown sugar, butter and sweet golden pineapple.
Here’s what you need:
- One box vanilla cake mix plus ingredients listed on the back of the box
- Butter
- Brown sugar
- Can of pineapple rings – you can also buy pineapple “tidbits”
- Pineapple juice (reserved from can)
- Small jar of maraschino cherries
To create that buttery, rich pineapple layer, start by combining melted butter and brown sugar. Drop a small spoonful in each muffin cup. Then arrange pineapple into “flowers” leaving a little space in the center for a cherry. I like to use the rings because I find the pineapple chunks to be too thick (tidbits will work but they’re a little smaller so you’ll need to use a few more per cupcake). Now, place half a cherry at the center of each of your “flowers”. Next, prepare the cake as according to the directions on the box with one exception. Substitute ½ cup of water with ½ cup of the reserved pineapple juice. Pour into each muffin cup and bake according to the recipe below.
To remove the cupcakes from the pan, run a sharp knife around the edge of each so they come loose. Now here’s the hard part – place a sheet pan over the top of the muffin tin then flip the whole thing over. The cupcakes should all come out easily. You may have to rearrange a few of the pineapple pieces.
Serve the cupcakes as is or jazz them up with whipped cream or caramel sauce. I personally love The Pioneer Woman’s Caramel Sauce Recipe.
Let me know what you think about this recipe in the comments section below. If you like this recipe, you may like Red Velvet Whoopie Pies
Kelsey Renee
Ingredients
- 2/3 cup butter
- 2/3 cup brown sugar
- 1 20 ounce can pineapple rings in juice
- Reserve ½ cup of pineapple juice
- 12 maraschino cherries
- 1 box vanilla or yellow cake mix (and ingredients listed on box)
Instructions
- 1. Preheat oven to 325 degrees and generously grease muffin tin(s). This recipe makes 24 cupcakes but you can bake them in batches if you only have one pan.
- 2. Melt butter in microwave safe dish. Stir in brown sugar until fully combined.
- 3. Add about a teaspoon of the butter/sugar mixture to the bottom of each muffin cup.
- 4. Cut each pineapple ring into 8 small wedges. Arrange 3 or 4 of the wedges into each muffin cup like a flower. It doesn’t have to be perfect.
- 5. Cut cherries in half. Place half a cherry in the center of each muffin cup in-between the pineapple wedges.
- 6. Prepare cake mix according to package directions but substitute ½ cup water with ½ cup pineapple juice.
- 7. Pour cake mix evenly over pineapples in each muffin cup.
- 8. Bake at 325 for 16-18 minutes. An inserted toothpick should come out clean.
- 9. Allow them to cool for 5 minutes.
- 10. Run a sharp knife around the edge of each muffin cup to loosen the cupcakes. Place a baking sheet on top of the muffin tin. Then, carefully flip over so that the pineapples are on the top.
- 11. Serve with whipped cream or caramel sauce.
- 12. Store in the refrigerator in an air tight container for up to 4-5 days.
Pin these Pineapple Upside-Down Cupcakes for later
Amber
My pineapple was still too long to fit in a cupcake pan and still fit the cherry (even though I used pineapple rings). I had to trim them down to fit. Also, make sure to put a cookie sheet on the rack below to catch any dripping! I learned the hard way that the brown sugar mixture bubbles out the sides and onto the bottom of my oven. Smoke billowing out! 😱
21 . Sep . 2019Linda Gamble
Pineapple to thick or big? I use crushed pineapple by mistake. It takes slightly more than a teaspoon spreader around the cherry. And the moistness is great!
23 . Oct . 2019Try it
Linda Gamble
Debbie
I made these for my son’s wedding reception. Delicious!!
06 . Dec . 2019