Cherry Pineapple Upside-Down Cake

The classic pineapple upside-down cake gets a retro twist with whole maraschino cherries tucked into every pineapple ring. Brown sugar melts into the butter at the bottom of the pan to form the glossy caramel topping, and the cake itself uses pureed pineapple and pineapple juice instead of milk. That swap keeps the crumb tender and amplifies the fruit flavor through every bite.

A quarter teaspoon of coconut extract is the secret. It’s a barely-there whisper, but it makes the cake taste tropical instead of generic-sweet.

This is a quick batter cake. Stir the wet into the dry only until just combined. Overmixing develops the gluten and turns an upside-down cake from tender to rubbery in about 30 seconds of extra stirring.

Pro Tips

• Use cake flour, not all-purpose. Cake flour has lower protein, which gives this cake its signature soft, fine crumb.
• Drain the pineapple slices well and pat dry. Excess juice on the rings turns the brown sugar layer into syrup soup instead of caramel.
• Invert the cake while still warm but not hot. Wait too long and the brown sugar caramel sets like glue, sticking the topping to the pan.
• Run a thin offset spatula around the edge before flipping to free any climbing batter.

Variations

• Swap maraschino cherries for fresh pitted cherries when in season.
• Add chopped pecans or macadamia nuts to the brown sugar layer for crunch.
• Use a 9-inch cast iron skillet instead of a baking pan for a more rustic, browned-edge result.