These Pineapple Upside-Down Cookies transform the classic cake into perfectly portable treats that capture all those beloved tropical flavors. Each soft, buttery cookie is crowned with a juicy pineapple chunk and a bright maraschino cherry, creating that signature upside-down cake look in cookie form. They’re perfect for parties, picnics, or whenever you want a taste of sunshine.
If you love these fruity flavors, you’ll adore our Hawaiian Banana Bread with Coconut & Pineapple for another tropical treat. For more cookie perfection, try our Strawberry & Lemon Blondies—they offer that same bright, fruity sweetness that makes these pineapple cookies so special.
Can’t get enough of great flavors? Check out these popular recipes that readers love making again and again.
For tropical-inspired treats, our Mini Pineapple Upside-Down Cheesecakes and Coconut Cream Bars bring that same sweet, fruity satisfaction. When you’re craving more cookie varieties, the Espresso Toffee Cookies and Blueberry Cheesecake Cookies deliver irresistible flavors in every bite. Need crowd-pleasing desserts? Our No-Bake Chocolate Eclair Cake and Cheesecake Brownies are always hit at gatherings.
Browse our full collection for more kitchen inspiration that’ll have your family asking for seconds.
















