1. In a large bowl, cream together the softened butter, granulated sugar, and brown sugar until light and fluffy.
2. Beat in the egg and vanilla extract until smooth.
3. In a separate bowl, whisk together flour, baking powder, and salt.
4. Gradually mix the dry ingredients into the wet until a soft dough forms.
Step 3: Assemble and Bake
1. Scoop about 2 tablespoons of cookie dough and gently press it over the pineapple in each muffin cup.
2. Bake for 18–22 minutes, or until the cookies are golden and set.
3. Allow to cool for 5 minutes, then carefully invert the pan onto a baking sheet or platter to release the cookies.
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Pro Tips for Perfect Pineapple Upside Down Cookies
Drain the pineapple well: Too much juice will make the topping soggy. Pat dry with paper towels.
Don’t skip the brown sugar: It caramelizes into a glossy glaze that makes these cookies irresistible.
Use a muffin pan: It helps the cookies keep their shape and holds the topping in place.
Invert while warm: The topping releases more easily before the caramel sets too hard.
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Serving Suggestions
These cookies are fantastic on their own, but you can elevate them by serving with:
A scoop of vanilla ice cream for a pineapple sundae twist.
A dollop of whipped cream for added lightness.
A sprinkle of toasted coconut for an extra tropical flair.
They pair perfectly with iced tea, piña coladas, or a simple cup of coffee.
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Why This Recipe is Loved
Portable and shareable: All the flavor of pineapple upside down cake in a cookie form.
Visually stunning: The glossy pineapple and bright cherry make them party-ready.
Easy to make: Simple ingredients, straightforward steps, and guaranteed crowd-pleasing results.
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Final Thoughts
These Pineapple Upside Down Sugar Cookies prove that a classic cake can be reimagined into a fun, handheld treat without losing its charm. They’re easy, flavorful,
and beautiful—perfect for any occasion. With their buttery cookie base and sweet pineapple topping, they’re guaranteed to disappear quickly.
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