A classic pineapple upside down cake with a buttery brown sugar caramel, juicy pineapple, and maraschino cherries, topped by a tender vanilla crumb. Simple ingredients and a forgiving method make it an easy, impressive dessert.
Prep Time 20 minutes mins
Cook Time 45 minutes mins
Total Time 1 hour hr 15 minutes mins
Dry the pineapple and cherries thoroughly to prevent a soggy topping. Use room-temperature dairy and eggs for even mixing. Do not overmix the batter; stop when no dry streaks remain. Invert the cake within 10–15 minutes so the caramel doesn’t stick. Store covered at room temperature for 1 day or refrigerate for 3–4 days; freeze slices up to 2 months. Reheat at 300°F (150°C) for 8–10 minutes. Variations: add cinnamon and nutmeg, swap some flour for shredded coconut, use fresh pineapple, or add 1–2 tablespoons dark rum to the juice. A 9-inch cast-iron skillet also works well.