There’s something unapologetically retro about a pineapple upside down cake. The glossy fruit. The brown sugar caramel. The dramatic flip at the end. It’s the kind of dessert that feels like it belongs in a cast iron skillet. And honestly, it does.
Upside down cakes rely on two things: steady heat and a pan that can move seamlessly from stovetop to oven. Cast iron handles both naturally.
The skillet melts the butter, caramelizes the sugar, and gently bakes the cake all in one place. Then, once everything cools slightly, you flip the whole thing onto a plate and let gravity do the final bit of work.
The result is a cake with crisp caramelized edges, tender crumb, and fruit that almost melts into the top. We especially love this version in the No.8 skillet. It’s the ideal size for getting enough height in the cake while still allowing the pineapple to caramelize properly around the edges.
Field Notes:
-
We strongly prefer fresh pineapple here. It has a firmer texture, brighter flavor, and less excess moisture, which helps the caramel stay rich instead of turning watery. Fresh pineapple also caramelizes more cleanly around the edges of the skillet.
That said, canned pineapple absolutely works if that’s what you have. If using canned rings or chunks, drain them very well and pat them dry with paper towels before arranging them in the skillet. You can also reduce the brown sugar slightly—about 1–2 tablespoons less—to account for the added sweetness in canned fruit.
The final cake will be a little softer and more nostalgic in the best way. Which, honestly, feels very appropriate for pineapple upside down cake.
- Want to make this with other fruits? Do it! This method works for fruits of similar textures like blackberries, raspberries and strawberries. If you try it with another fruit, let us know how it goes!
Print Recipe
