Pineapple Upside Down Cupcakes

I love pineapple upside down cake, but I hate making entire cakes. I don’t like making a mess slicing pieces, and cakes don’t get eaten with only two people in the house. So I decided to make cupcakes!

Right after I made the batter I thought of the reason people don’t really make pineapple upside down cupcakes–the puff at the top of the cupcake will make it weird when you flip it over! Thankfully this particular recipe doesn’t rise much; as long as you don’t fill the cupcake tins up to the top they should be fine! They don’t look as much like cupcakes as they do mini-cakes.

My dad told me how to make pineapple upside down cake, and I used a Better Homes and Garden cookbook for the yellow cake itself.

This is the recipe my dad emailed to me. Joseph commented that he types exactly the way he speaks.

Topping:
Brown sugar
Butter
1 can pineapple slices (reserve juice)
Maraschino cherries
Pecans (optional)

Melt butter and brown sugar for a few minutes in the oven. I spooned a small amount of brown sugar into each cupcake tin and wish I had used more because they weren’t as caramelized as I would have liked. Mine definitely did not add up to a cup like my dad suggested, so don’t be shy on the sugar.  I would guess a tablespoon for each cupcake would be good.
Arrange pineapple slices, cherries, and pecans if using them. I opted out of the pecans because I don’t like them much.
Pour cake batter gently and evenly–remember the fruit might be moved around a bit.

Cake:
¾ cup butter
3 eggs
2 ½ cups all-purpose flour
2 ½ tsp baking powder
½ tsp salt
1 ¾ cups sugar
1 ½ tsp vanilla
All reserved pineapple juice, plus enough milk to add up to 1 ¼ cups

Allow butter and eggs to stand at room temperature for 30 minutes. Stir together flour, baking powder, and salt; set aside.

Preheat over to 375F. In a mixing bowl beat butter with an electric mixer on medium to high for 30 seconds. Gradually add sugar, beating until well combined. Beat 2 minutes more. Add eggs one at a time, beating well after each addition. Beat in vanill. Alternately add flour mixture and the pineapple juice and milk mixture, beating on low speed after each addition just until combined. Gently spread into prepared and greased pans.

Bake for 20-25 minutes for cupcakes or 9-inch pans, 30-35 minutes for 8-inch pans, or 25-30 minutes for 13×9x2 pan. Let cool for ten minutes and flip onto baking sheet.

Here’s a bad picture I took a few years ago of a pineapple upside down cake I made. You can see I used a full cup of brown sugar, so it caramalized more: