I remember growing up that having a Pineapple Upside Down cake was always a special treat. For some reason, I grew up thinking that it was some sort of difficult recipe to make. I mean it had to be right? You had to magically make this cake that after you baked it and inverted it that there were these pineapples and cherries perfectly and symmetrically placed on the, now top, of this cake. It was like some sort of magic.
I can’t be the only one who thought this growing up was I?
Fast forward to about a year ago, and I finally realized that not only was this sort of cake insanely easy to make, but that making your own cake batter (no, not out of the box) was really easy as well. WHY HAD I NEVER TRIED TO MAKE A CAKE FROM SCRATCH BEFORE!? Annnndddd….why did I not know that there were other fruit combinations to make upside down cakes with!? WHYYY had people been hiding this secrecy from me!?
My vow to my girls —>>> make all the upside down cake things while they are growing up.
Last Christmas, we went over to Andrew’s brothers house and his sister had made pineapple upside down cupcakes.
WHATTTT!?
Again, I was left with this feeling of why? Why did I not know or even think of this before? So, I was determined to make them at home. This recipe make 12 large cupcakes, so if you wanted them smaller you could definitely adjust for that. They would be adorable as mini cupcake bites. We use strawberries in this recipe instead of cherries because not only is the flavor combination delicious, but *most* store bought cherries have a ton of red dye in them and we try to avoid dyes in our home. Also, because I once saw a documentary on how maraschino cherries are made and it weirded me out HAHA.
Anywho…. We made a family day out of this one and we all pitched in to help make these Pineapple Upside Down Cupcakes. Well, Baby just really enjoyed screaming until someone put more food in her mouth. Skibbles was so confused about why we were putting fruit in the bottom of the pan when I told her we were making cake and kept saying, “no, mama, I want cake”. Luckily, she eventually saw that we really were making pineapple upside down cupcakes and the meltdown didn’t last too long.

- 1 1/3 cup flour
- 1/2 cup unsalted butter melted, divided
- 1/2 cup whole milk
- 1/4 cup vanilla greek yogurt
- 3/4 cup brown sugar + 1 tbsp divided
- 1/4 cup white sugar
- 1/2 tbsp vanilla extract
- 1 1/2 tsp baking powder
- 1/4 tsp salt
- 1 egg
- 1/2 pint canned pineapple finely chopped (1/2 can crushed if store bought)
- 3 large strawberries halved
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*For the following recipe, we made 6 large cupcake. Adjust accordingly to make smaller ones.
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Preheat oven to 350 degrees.
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In the bottom of each cupcake tin, brush 1/4 cup melted butter evenly amongst the 6 tins.
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Evenly divide pineapple in a ring along each tin and place one half of a strawberry in center of pineapple.
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Take 1 tbsp brown sugar and evenly sprinkle on top of pineapple/strawberry mixture.
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In a bowl, mix remaining dry ingredients together with a whisk.
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Then add wet ingredients and whisk together until no lumps remain.
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Evenly divide mixture to each tin.
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Bake 25-28 minutes or until golden brown and toothpick inserted comes out clean.
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Remove and let sit for 3 minutes.
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Invert pan onto a baking sheet and carefully remove.
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Let cool, serve immediately.
Don’t they just look delicious!? What other flavors of “upside down” desserts have you made?
I am hosting Mini Chef Mondays along with 8 fabulous bloggers! Read how Mini Chef Mondays started, plus how to link up!
Join our facebook group to find even more recipes and share recipes too!
Be sure to check out each of their Mini Chef posts as well!
- Banana Split Smoothie // Courtney’s Sweets
- Old Fashion Lemonade Recipe // Momma Lew
- Homemade Limeade // Baby Loving Mama
- Pineapple Upside Down Cupcakes // We’re Parents
- Encouraging Fruits and Vegetables for Kids // Eating Richly Even When You’re Broke
- Cookies & Cream Milkshake // Giggles, Gobbles and Gulps
- Easy Spinach Manicotti // Vegging at the Shore
- Make Your Own Omelette Bar // O’Boy! Organic
- Dinosaur Fossil Cookies // Can’t Google Everything