Ingredients
Equipment
Method
- Position oven rack in the middle and heat to 350°F (175°C), then lightly grease only the sides of a 9-inch (23cm) round light-colored aluminum cake pan with butter or non-stick spray.
- Scatter the ⅓ cup (75g) unsalted butter pieces evenly across the bottom of the pan, then sprinkle the ½ cup (110g) packed dark brown sugar evenly over the butter in a single layer — do not stir or press down.
- Place the pan in the refrigerator while you prepare the fruit — approximately 5 minutes.
- Drain the canned pineapple rings and reserve the juice in a measuring cup, then pat the rings dry between paper towels and arrange them in a single layer across the brown sugar base — one ring in the center, remaining rings fitted snugly around it.
- Drain the maraschino cherries and pat them dry between paper towels, then place one cherry in the center hole of each pineapple ring and tuck additional cherries into the gaps between rings.
- In a large mixing bowl, whisk together the ¾ cup (180ml) reserved pineapple juice, 3 room temperature eggs, and ½ cup (113g) melted and cooled butter until smooth and uniform — approximately 20 to 30 seconds.
- Add the full box of dry yellow cake mix and fold with a silicone spatula using slow strokes from the bottom of the bowl upward — approximately 40 to 50 strokes — until no dry streaks remain; do not overmix.
- Pour the batter slowly and evenly over the fruit layer starting at the center and working outward, then use the spatula to spread it gently to the edges without disturbing the fruit arrangement below.
- Bake at 350°F (175°C) for 40 to 45 minutes until a toothpick inserted in the center comes out clean or with a few moist crumbs and the top surface is deep golden brown and pulling from the pan sides.
- Remove from oven and set on a wire rack for exactly 10 minutes — set a timer — then run a thin knife around the inside edge of the pan, place a large flat serving plate face-down over the pan, and flip in one confident motion; lift the pan straight up and reposition any fruit that shifted.
- Serve warm with any caramel that pooled on the plate spooned back over the slices.
Notes
- Pineapple: must be canned sliced rings in juice — not fresh (bromelain enzyme prevents the cake from setting), not canned in syrup (too sweet), not frozen.
- Butter — caramel base: goes in cold and in pieces, not pre-melted — slow release keeps the sugar from scorching before the cake sets.
- Butter — batter: melt and cool for at least 5 minutes before adding eggs — hot butter scrambles the eggs on contact.
- Brown sugar: pack firmly into the measuring cup — loose brown sugar produces a thin, pale glaze.
- Cherries: drain and pat completely dry before placing — wet cherries bleed dye into the caramel layer.
- Pan: light-colored aluminum only — dark non-stick pans scorch the caramel base before the cake bakes through. Do not use a springform pan — the caramel base will leak.
- Inversion timing: flip at exactly 10 minutes — too early and the caramel is still liquid, too late and it bonds to the pan.
- Storage: store loosely covered at room temperature up to 2 days, or refrigerated up to 5 days — never wrap tightly.
- Freeze: freeze individual slices wrapped tightly in plastic wrap up to 6 weeks — thaw overnight in refrigerator, reheat at 300°F (150°C) for 8 to 10 minutes.
- Make ahead: bake up to 24 hours ahead — reheat whole cake at 300°F (150°C) for 12 to 15 minutes before serving.
- Scaling: to make in a 9x13 pan, use 2 cans pineapple and 1.5 jars cherries — same butter and brown sugar quantities — reduce bake time to 30 to 35 minutes.
- Altitude: start checking at 35 minutes at high altitude — leavening in the cake mix activates faster above 3,500 feet.
- Allergens: contains gluten, dairy, and eggs.
- Tip: pour any caramel that pools on the serving plate back over the slices before serving — it is the most concentrated, deeply flavored part of the glaze.