Imagine the nostalgic charm of a soft, buttery sugar cookie—now kissed with the bright, caramelized sweetness of pineapple and a hint of cherry, just like the iconic cake that inspired it.
These Pineapple Upside-Down Sugar Cookies are the perfect blend of classic comfort and tropical flair. They’re soft, chewy, and studded with juicy pineapple bits, then topped with a maraschino cherry for that unmistakable retro look.
No cake pan required—just your favorite cookie sheet and 20 minutes of baking time!
Why You’ll Love This Recipe
🍍 Fun, nostalgic twist on two beloved desserts
⏱️ 30-minute prep, then bake
💰 Budget-friendly—uses pantry staples + canned fruit
❤️ Kid-approved & potluck-perfect
🌟 Looks impressive—golden edges, fruity centers, cherry on top!
“It’s not fancy—but it tastes like a vacation in every bite.”
Ingredients You’ll Need
(Makes 24 cookies)
For the Cookies:
2¾ cups (345g) all-purpose flour
½ tsp baking soda
¼ tsp salt
¾ cup (1½ sticks) unsalted butter, softened
1 cup granulated sugar
1 large egg, room temperature
1 tsp vanilla extract
½ cup crushed pineapple, well-drained (canned is fine!)
For the Topping:
24 maraschino cherries, stems removed
2 tbsp reserved pineapple juice (optional, for glaze)
💡 Pro Tip: Drain pineapple in a fine-mesh sieve, then press with a spoon to remove all excess liquid—wet dough = flat cookies!
Step-by-Step Instructions:
