Pineapple Upside Down Cookies - The Stay At Home Chef

These Pineapple Upside Down Cookies are the perfect sweet treat to satisfy your sweet tooth and are surprisingly easy to make! You get the delicious, caramelized pineapple that you love from the classic cake recipe, but in cookie form. Juicy pineapple and cherries not only give these cookies a sweet, fruity flavor but also makes them soft and moist long after coming out of the oven.

For more pineapple treats, try the original with a classic Pineapple Upside Down Cake.

Why Our Recipe

Craving pineapple upside-down cake? Satisfy that craving in cookie form instead!
Tropical flavors make us feel like we’re on vacation with this sweet treat.
Caramelized pineapple and juicy cherries make this cookie super soft and moist.

These homemade cookies really have it all. You get juicy freshness from the pineapple ring, a little pop of cherry flavor in the middle, all topped with a soft, buttery cookie. We use brown sugar to candy the pineapple, giving it a delicious caramelized flavor and texture. You won’t be able to eat just one!

Ingredient Notes

Ingredients used to make Pineapple Upside Down Cookies.

Pineapple Rings: We use canned pineapple rings. Drain to remove excess moisture before using!
Maraschino Cherries: Drain and half these cherries before placing in the pineapple ring.
Brown Sugar: Separated into two parts: 3/4 cup for the dough and 1/2 cup for the candied pineapple.
Butter: If you only have unsalted on hand, just add a 1/2 tsp salt to the dough. Be sure it’s softened to room temperature before creaming.
Vanilla Extract: Pure vanilla extract gives the best flavor, but imitation vanilla also works.
Eggs: Use large eggs at room temperature for easier mixing.
All-Purpose Flour: Stick with regular all-purpose flour for this one. Bread flour can also work.
Baking Powder & Baking Soda: Check the expiration date to ensure proper leavening.

Dark Brown Sugar vs Light

Dark brown sugar has a higher molasses content compared to light brown sugar, which intensifies its flavor a little bit and adds extra moisture. Dark brown sugar achieves a deeper caramel-like richness and a chewier texture. And the cookies end up staying soft for just a little bit longer.

Collage of Pineapple Upside Down Cookies showing process of making them.

Candied Pineapple

Candy-ing the pineapple in these cookies is a crucial step you won’t want to skip. The brown sugar and natural sugars in the fruit work together to caramelize, giving that pretty golden brown color and delicious, warm caramel flavor.

After placing your pineapple rings and cherries on the parchment paper, sprinkle about a spoonful of brown sugar on each ring. Don’t worry if you add a little too much and some brown sugar spills out on the sides. This gives you a nice little crunchy, caramel crisp on the outside that we’re not mad at!

Pineapple Upside Down Cookies sitting on a marble platter.

These pretty cookies are practically perfect on their own, but if you want to get creative, we’re all for it. Here are some suggestions for customizing this cookie:

White chocolate chips give extra sweetness and texture; feel free to mix in about a 1/2 cup to the dough.

Sweetened coconut flakes are also a great option to pair with the pineapple. Add about a 1/4 cup to the dough or toast and sprinkle on top.