Pineapple & Cherry Butterscotch Cake

This is a classic pineapple upside-down cake with a butterscotch twist. A thick layer of brown sugar lines the bottom of the pan with dots of butter, creating a sticky, caramelized base that becomes the glossy top when you flip the cake out.

Pineapple rings arranged over the brown sugar with a maraschino cherry tucked into each center is the iconic look. During baking, the fruit caramelizes in the butter and brown sugar, turning golden and jammy.

The cake batter is a straightforward creamed shortening recipe: sugar and shortening beaten together, eggs added, then flour and milk alternated in. This alternating method keeps the batter smooth and produces a tender, even crumb that’s sturdy enough to support the heavy fruit topping without collapsing.

Turn the cake out onto a plate immediately after baking. Wait too long and the brown sugar hardens, fusing the cake to the pan. One confident flip while it’s still hot and the whole thing releases cleanly.

Serve warm with whipped cream and extra cherries on top.

Chef Tips

• Pack the brown sugar about ½ inch deep across the bottom of the pan. This generous layer is what creates the butterscotch sauce.
• Grease the pan well before adding the brown sugar. Even with all that butter, you need the pan itself to be non-stick.
• Pat the pineapple rings dry before placing them in the pan. Excess juice dilutes the butterscotch.
• Use a 10-inch round pan as specified. A smaller pan will overflow during baking.

Variations

• Use dark brown sugar instead of light for a deeper, more molasses-rich butterscotch flavor.
• Add chopped pecans between the pineapple rings for a nutty, crunchy topping.
• Replace pineapple rings with sliced fresh peaches for a seasonal summer version.