Pineapple Upside-Down Cupcakes

One week to Caleb's birthday. The coconut cakes are made: the smash cake in its small round pan, the sheet cake in the good pan I use for special occasions. Both are in the freezer now, unfrosted, waiting for Saturday. I will frost them Friday evening so they are fresh. The Italian meringue buttercream is already made and waiting in the refrigerator in a sealed container.

CJ called Tuesday evening and I could hear Caleb in the background — a persistent vocal presence, a series of sounds that are organizing themselves toward syllables. He says Mama and Dada with clear intent now, and what CJ insists is Nana and what Shanice insists is a generalized appeal for food, and what I know to be both. He also says something that sounds like hot when he reaches for things he shouldn't touch, which means Shanice has been saying the word consistently near the stove and he has absorbed it as a category: things that are not for Caleb. He knows. He reaches anyway. He is methodical and stubborn. He is completely his father's son.

I drove to Huntsville Friday. CJ met me at the door and carried my bags and the cake box with the same care you give things that cannot be replaced. I set the cakes on the kitchen counter and stood back and looked at them: the coconut sheet cake and the little smash cake beside it, ready for tomorrow. Caleb came around the corner on his hands and knees and looked up at the kitchen counter with great interest. He could not see the cakes. He could smell them. He sat back on his heels and made his sound for: this requires investigation. I told him he would have to wait until tomorrow. He considered this assessment. He did not appear to accept it but he let it stand.

Caleb could smell those coconut cakes through a sealed box, which tells you everything you need to know about why I believe in making individual portions when little ones are involved — something sized just for them, something they can fully claim. These pineapple upside-down cupcakes have that same quality: each one is its own small celebration, caramelized and golden on top, the kind of thing a one-year-old would absolutely reach for if given half the chance. I’ve been making them alongside the birthday cakes when the occasion calls for guests who want something they can hold in one hand while the birthday boy holds his own.

Prep Time: 20 min | Cook Time: 22 min | Total Time: 42 min | Servings: 24 cupcakes

Ingredients

1/2 cup unsalted butter, melted
1 cup packed light brown sugar
1 can (20 oz) crushed pineapple, well drained (juice reserved)
24 maraschino cherries, stems removed
1 box (15.25 oz) yellow cake mix
3 large eggs
1/3 cup vegetable oil
Reserved pineapple juice plus water to equal 1 cup

Instructions

Preheat and prepare. Preheat oven to 350°F. Line two standard 12-cup muffin tins with foil baking cups (foil liners hold their shape when inverted; paper liners do not).
Make the topping. Stir together the melted butter and brown sugar. Spoon about 1 tablespoon of the mixture into the bottom of each foil-lined cup, spreading it evenly.
Add fruit. Place one maraschino cherry in the center of each cup. Spoon a heaping tablespoon of well-drained crushed pineapple around the cherry in each cup.
Mix the batter. In a large bowl, beat together the cake mix, eggs, oil, and the reserved pineapple juice mixture on medium speed for 2 minutes, until smooth and well combined.
Fill the cups. Spoon the batter over the fruit layer in each cup, filling each about two-thirds full.
Bake. Bake for 20–22 minutes, until a toothpick inserted in the center of a cupcake comes out clean and the tops are set and lightly golden.
Cool and invert. Let cupcakes cool in the pan for exactly 5 minutes — no longer or the caramel will stick. Place a large wire rack or baking sheet over each pan and carefully flip. Lift the pan away and allow the cupcakes to cool completely, fruit side up.
Serve. Peel away the foil liners just before serving. The caramelized pineapple and cherry topping should be glossy and intact. Serve at room temperature.

Nutrition (per serving)

Pineapple Upside-Down Cupcakes — The Little Cake That Has to Wait Until Tomorrow