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These Pineapple Upside‑Down Sugar Cookies transform the nostalgic flavor of pineapple upside-down cake into soft, handheld sugar cookies with tropical charm and a delightful pineapple topping.
2 cups all-purpose flour
1 teaspoon baking powder
1/4 teaspoon salt
3/4 cup unsalted butter, softened
1 cup granulated sugar (plus extra for rolling)
1 large egg
1 teaspoon vanilla extract
1/2 cup pineapple jam or crushed pineapple (well drained)
Optional: small pineapple slices or rings for garnish
Optional: sanding sugar for rolling
Chill dough to prevent cookies from spreading too much.
Drain crushed pineapple thoroughly if using instead of jam.
Top with a cherry for a retro look.
Sprinkle coarse sugar for added texture.
Drizzle with cream cheese glaze for extra sweetness.