Equipment Needed
- Standard 12-cup muffin tin
- Cupcake liners (optional, but helpful for cleanup)
- Small saucepan
- Mixing bowls (medium and large)
- Whisk
- Measuring cups and spoons
- Cooling rack
- Small spoon or brush
Step-by-Step Instructions
First, we’ll create the iconic topping. Melt 4 tablespoons of the butter in a small saucepan over medium heat. Stir in the brown sugar and 2 tablespoons of the reserved pineapple juice until it looks like a thick, glossy sauce. This is the magic glue. Remove it from the heat. Now, prep your muffin tin. I strongly recommend using liners for easier cleanup. Place one maraschino cherry in the center of each cup. Cut your pineapple rings into small wedges or pieces—I find about 4-6 pieces per ring works perfectly—and arrange them around the cherry. Carefully spoon the warm brown sugar butter evenly over the fruit in each cup. This layer will become your gorgeous, sticky top, so be generous!
Now, for the cake batter. Preheat your oven to 350°F (175°C). In my medium bowl, I whisk together the flour, baking powder, and salt. In my large bowl, I beat the remaining 4 tablespoons of softened butter with the granulated sugar until it’s light and fluffy. This takes a good 2-3 minutes with a hand mixer—don’t rush it, as this creates air for a tender cake. Beat in the eggs, one at a time, followed by the vanilla. The mixture should look smooth and pale.
Here’s where we combine everything. Add about a third of your dry flour mixture to the butter bowl and mix on low until just combined. Follow that with half of the milk. Repeat, ending with the last third of the flour. Finally, stir in 2 more tablespoons of that precious pineapple juice. The batter will be thick, smooth, and wonderfully fragrant. I use a large cookie scoop or two spoons to divide the batter evenly over the fruit layer in each muffin cup, filling them about 2/3 to 3/4 full.
Bake for 20-25 minutes. The real test is when the tops are golden and spring back lightly when touched. I learned the hard way that a toothpick test can be misleading if you hit a juicy pineapple pocket! Let the pan cool on a rack for only 5 minutes—this is crucial. Any longer and the caramel will harden and stick. Place a cooling rack or a large baking sheet over the tin and, with confidence (and oven mitts!), flip the whole thing over. Give it a gentle tap and slowly lift the tin. That reveal is the best part of my baking week.(See the next page below to continue…)