Rooted in the vintage Dinette Cake batter tradition found in Betty Crocker cookbooks of the 1960s and 1970s, this classic pineapple upside-down cake recipe pairs a caramelized dark brown sugar and butter topping with a tender, oil-based vanilla cake batter that produces a soft, fluffy crumb and releases cleanly from the pan every time. Dole’s 1925 recipe contest first made pineapple upside-down cake a household staple, and this scratch-made version preserves everything that made the original worth making for the next hundred years.