Ingredients:

  • For the Topping:
  • Unsalted butter, 1/4 cup (56 g), melted
  • Packed light brown sugar, 1/2 cup (100 g)
  • Pineapple rings, 1 (20 oz / 567 g) can, drained (reserve juice if desired)
  • Maraschino cherries, 8-10 (optional)
  • For the Cake Batter (box mix base):
  • Yellow cake mix (regular size), 1 box (15.25 oz / ~432 g)
  • Water, 1 cup (240 ml) — or follow package directions
  • Vegetable oil, 1/3 cup (80 ml) — or follow package directions
  • Large eggs, 3 — or follow package directions
  • Optional enrichments (add to batter if desired):
  • Vanilla extract, 1 tsp (5 ml)
  • Sour cream or plain yogurt, 1/2 cup (120 g) — for extra moistness (reduce water a little if using)

Instructions:

  1. Preheat oven to 350°F (175°C). Grease a 9-inch round cake pan (or 9–10 inch cast-iron skillet) well with butter and a light dusting of flour or non-stick spray; optionally line the bottom with a round of parchment.
  2. Make the caramel topping by combining the melted butter and packed brown sugar directly in the prepared pan; spread into an even layer so the mixture is glossy and uniformly distributed.
  3. Drain pineapple slices very well and blot if needed. Arrange pineapple rings in a single layer over the brown sugar mixture, placing maraschino cherries in the centers or between slices as desired. Pieces should sit on top of the caramel, not submerged.
  4. Prepare the cake batter: in a mixing bowl, combine the boxed yellow cake mix with water, vegetable oil, and eggs according to package directions. Optionally stir in vanilla extract or sour cream/plain yogurt for extra richness. Mix just until combined and smooth; avoid over-mixing.
  5. Spoon or gently pour the batter over the arranged pineapple, spreading carefully to cover fruit evenly. Tap the pan lightly to settle the batter and remove air pockets.
  6. Bake at 350°F (175°C) for 35–40 minutes, or until a toothpick inserted in the center comes out with a few moist crumbs and the cake is pulling slightly from the pan edges. Edges will be golden and the caramel may bubble at the perimeter.
  7. Cool and invert: let the cake cool in the pan on a rack for 8–12 minutes. Run a knife around the edge to loosen, place a serving plate over the pan, and invert quickly but carefully. Lift the pan off; spoon any caramel bits back into place if needed. Allow to cool slightly before slicing.
  8. Serve warm or at room temperature. Optionally top with whipped cream or a scoop of vanilla ice cream.