Cake Mix Pineapple Upside Down Cupcakes

These muffin tin pineapple upside down cupcakes are one of our favorite boxed cake mix recipes. Mini size cakes you can make using ingredients from the Dollar Store. If you love muffin tin recipes this is a fun one to try.

We're a little obsessed with our muffin pan. We have cooked almost everything in them! When it comes to desserts we love using muffin pans mostly because it skips the messy cutting step, and they are already made into portions for each person…plus kids love it! Here is our easy recipe for pineapple upside down cupcakes.
We do love making our easy pineapple upside down cake with yellow cake mix in a bundt pan, but once again it's messy. This is a great way to get that same great taste but in already portioned cakes. We use our large muffin pan for this recipe.
Get your kids involved in this one because they will feel successful once they are done. Baking in a muffin tin is great. It doesn't take long to cook and are already individual servings so you don't have to slice anything.

Can you make pineapple upside down cake in a muffin tin?
Yes! This is what we are going to show you here. We have made this classic dessert all sorts of ways over the years. Of course when you use a larger pan you use pineapple rings whole, this time you will need smaller pieces so they fit in the bottom of each muffin tin hole.
What we like to do is reserve the pineapple juice for extra flavor. Some boxed mixes require a bit of water. Instead of that we will use the juice! Then since we hate to waste we will drink the rest, or make a glass of our favorite pineapple cocktail. We mean…..it would be tragic if you didn't do something with it right??
To make an easier cleanup, and cuter if you buy patterned ones, you can use cupcake liners inside. They will turn out wet on the bottom so keep that in mind if you do. The silicone versions are best because of that issue. OR use some cooking spray in each hole so all the goodness slides right out.

We bought all the ingredients at the Dollar Store this time, and bought double to make pineapple casserole too. They cost us a whopping $3 for everything! We had a stick of butter at home already in this case but several times we have even found that in their refrigerated section. For a dairy free version use plant based butter product and that works too. This is what you will need.
What Kind of Cake Mix to Use
To make this super easy and fast to make we are going to start off the dry ingredients with a box of Yellow cake mix + items to make the batter which is typically egg and water. You could use any flavor you'd like but this is traditionally used unless you can find pineapple flavor.
Maraschino cherries are the ones in the jar, you want one per hole basically. You could actually use the juice to substitute some of the water used to make the cake batter for a sweeter outcome and pink color.
Melted Butter will be on the bottom to keep it moist, we like salted Kerrygold for the best flavor and creaminess with some Brown sugar to keep it sweet/
You will want small Pineapple chunks or tidbits work to add to the bottom with the batter on top so when flipped over it will be on the top when served.
Can you use crushed pineapple?
You could, the look would be different when you flip it over and there is more juice so it may be a bit more wet on the top/bottom. What we would do in that case is to drain the can as much as possible and add about 1 tsp into each hole.

How Long to Bake Pineapple Upside Down Cupcakes
Once you have the batter created as directed on cake mix box and a ready preheated oven you will want to bake once assembled for about 15 – 18 min. or until top springs back when touched gently in the center. Allow to cool in pan for 10 minutes before scooping out with a spoon or flipping over on to a cutting board.
How do you know when they pineapple upside down cupcakes are done?
The way we ensure these are done is to not necessarily use a toothpick inserted until dry. Sometimes you can over-bake them this way. Instead use your finger. Pull the pan out a bit and gently touch the center of a few of them. If they spring back then you want to pull them out immediately. The biggest thing is you don't want them to dry out.
In the case that you touch one and it doesn't pop back up but rather stays down then it needs another 2 minutes or so. Give it that bit of time and then check again this same way. These are great served still warm right out of the oven with a bit of whipped cream after you've flipped them over on to a plate.
Frosting
If you wanted some frosting mix some confectioners sugar with a little water. This will make a quick glaze to drizzle over the top when they are done and you're ready to eat. When they come out scoop each one out, flip it over and drizzle with frosting.
Pineapple Upside Down Cupcakes Recipe
By Pynmi EASY cake mix pineapple upside down cupcakes in a muffin tin instead of cake is fun to cook with kids and costs $3.00 total for the whole recipe with ingredients from The Dollar Store. Prep: 5 minutes minsCook: 18 minutes minsTotal: 20 minutes minsServings: 18 Save Recipe Saved! Pin Recipe Comment Print Recipe
Equipment
Ingredients
- 1 box cake mix, we used yellow, make as directed on box
- 1 jar maraschino cherries
- 1 can pineapple, sliced or chunk, save juice to use in cake batter – 4 1" pieces per hole
- 6 tbsp butter melted
- 3/4 cup brown sugar
Instructions
- Make yellow cake mix as directed (for deeper pineapple flavor use pineapple juice in place of water if that is needed in directions). Spray your muffin pan with non stick spray (we wouldn't use paper liners)
- Melt butter and then whisk together with brown sugar. Spoon 1 tbsp into each muffin tin hole + 2-3 pieces of pineapple tidbits + 1 cherry in middle + pour batter on top of that (fill to 3/4 of the way full for each muffin hole).
- Bake in preheated oven at 350 degrees for approx. 15 -18 min. or until top of cupcake springs back when touched gently in the center.
- Cool tin on a cooling rack for 10 minutes before scooping out with a spoon or flipping pan over on to a large cutting board.
Nutrition
Nutrition information is automatically calculated, so should only be used as an approximation.
Additional Info
Course: Breakfast, DessertCuisine: American Tried this recipe?Mention @thetypical_mom or tag #thetypicalmom!Do you eat pineapple upside down cake warm or cold?
We mean that is personal preference but we let it cool a bit before flipping, add a bit of glaze and enjoy warm after dinner. If you have never enjoyed baked fruit it is actually quite good with a while different flavor than cold.
Do you have to refrigerate leftovers?
When they are done if you have leftovers we would keep them in an airtight container and in the fridge. If you have quite a few place a piece of waxed paper in between the layers so they don't stick together and become a lumpy clump together.
Since there is fruit in there you don't want it to get soggy and kinda' an ewy texture on the outside. Keeping it cool will kinda' prevent this issue. The next day you'll want to add more frosting and microwave for 45 seconds. Then enjoy again!
Other easy desserts you'll love
Ourpear upside down cake is fabulous. We've made Instant Pot pineapple upside down cake too! Use another fruit to make banana upside down cake some time too




