Easy Pineapple Upside Down Cupcakes

5 from 20 votes

Tender vanilla cake topped with a rich caramel sauce and juicy fruit. If you like the cake you'll go crazy over the cupcakes!

Course Dessert

Cuisine American

Prep Time 10

Cook Time 18

Total Time 28

Servings Cupcakes

Calories 410kcal

Preheat oven to 350 degrees F. Spray a mini Bundt pan with non stick baking spray.
In a medium bowl, combine brown sugar and melted butter. Divide between muffin tins. Also, add one pineapple slice and one cherry to each.
In a large bowl, combine flour, salt, and baking powder.
In another large bowl, cream butter and sugar until light and fluffy. Add vanilla, and eggs one at a time.
Alternate adding in flour mixture and milk until everything is just combined.
Divide evenly between prepared pans. Bake for 18-22 minutes.
Cool before flipping over.

Ingredient Notes:

- Flour: Measure your flour by spooning it into a measuring cup and leveling it with a spoon. Avoid dipping your cup into the flour as you'll likely use too much, which will lead to a dense, dry cake.
- Butter: You want your butter to be softened but not melted. If your finger makes an indent when you press it, it is ready to use.
- Pineapple: Be sure to drain in a strainer to remove excess moisture. Then pat dry with paper towels. I would not suggest using fresh pineapple here as it may be too juicy.
- Marachino Cherries: These can be tricky to find at the store. Try looking in the cocktail mixer section or near the ice cream cones.

Tips

Don't Overbake: Cupcakes are done when a toothpick inserted in the center comes out with a with just a few moist crumbs. It's okay if it's not totally clean.

Don't Overfill: Fill your cupcake pan only around ⅔ of the way full. They'll rise as they bake. You don't want them to overflow and make a mess!
Perfect Flipping: I suggest turning them upside down onto a baking sheet or wire rack around 5-10 minutes after removing them from the oven. If they don't come out immediately, let gravity do its work. You can also try gentling and loosening with a butter knife.