This pineapple upside-down cake delivers everything you want from the retro classic—sticky, buttery caramel; glossy, jammy fruit; and a tender, plush crumb—plus a few smart upgrades.

Cookbook author Cheryl Day swaps in deeply flavorful Luxardo cherries for the usual neon maraschinos, bringing a richer, almost winey sweetness that plays off the bright tang of pineapple. And instead of fussing with fresh fruit, this recipe leans on canned pineapple rings (packed in 100% juice) for their consistent shape, reliable juiciness, and picture-perfect finish.

The payoff is in the flip. Once inverted, the brown sugar–butter topping reveals a mosaic of caramelized fruit that glazes the cake as it settles.…