Pineapple Upside-Down Cookies

How To Make Pineapple Upside Down Cookies

Using Betty Crocker™ Sugar Cookie Mix makes these pineapple upside-down cake cookies quick and easy to pull together. Here, we’re outlining the steps to making these impressive cookies, but for the full list of ingredients and directions, refer to the recipe below.

Prepare the Fruit

Drain the canned pineapple rings on a paper towel-lined tray. Transfer seven rings to each of two parchment paper-lined cookie sheets, spacing evenly to allow at least 2 inches between rings. Place a cherry on the center of each ring.

Prepare the Cookie Dough

In a bowl, mix together the sugar cookie mix, vanilla pudding mix, butter, brown sugar, egg, vanilla, and pineapple juice (reserved from can) until soft smooth dough forms.

Form the Cookies

Using about 3 tablespoons of dough, roll dough between palms of hands to shape the cookie dough into 2-inch balls. Place a dough ball on top of each pineapple ring, then flatten slightly.

Bake, Cool, and Flip

Bake the cookies about 25 minutes on parchment-lined cookie sheets in a 350°F oven. You will know they are done with the tops are cracked and golden brown. Cool cookies on cookie sheets for 10 minutes to set up. Carefully remove the pineapple upside-down cookies from the cookie sheets with a spatula, flipping over to cool completely on cooling rack.

Storing Pineapple Upside Down Cookies

These pineapple upside-down cookies can be stored at room temperature in a single layer on a plate or tray, covered with waxed paper (or loosely covered in some way). They’re best enjoyed the day they are baked. If this pineapple upside-down cookie recipe is made too far in advance, the moisture from the fruit will continue to be absorbed into the cookie, making it wet and fragile. For that reason, we don’t recommend serving this cookie more than 1 day after baking.

Just like a pineapple upside-down cake, freezing is not recommended. The pineapple will not hold up to the well to the freezing and thawing process. The texture of the cookie will be compromised.

Variations

We tested this pineapple upside-down cookie using both canned pineapple rings and canned pineapple chunks. Both worked well in the cookies. Fresh pineapple is not as consistent in texture, moisture and sweetness, which is favored for pineapple upside-down desserts.

Pineapple rings: We found canned pineapple rings to the be the best option for this recipe because they are consistent in texture, moisture and sweetness.

Pineapple chunks: Great option for making mini pineapple upside-down cookies. The canned chunks provide the fun mini size while retaining the desired texture and flavor.

Fresh pineapple: Although we love fresh pineapple, it just isn’t the best option for these cookies. It is not as consistent in flavor, moisture level or texture as canned.

For mini pineapple upside-down cookies, drain 1 can (20 oz) pineapple chunks; cut each chunk in half (you will have some left over). Cut 10 maraschino cherries in half. For each cookie, place 1 cherry half on pan and arrange about 5 pineapple pieces in tight circle around cherry. Make dough as directed in recipe below, except form dough into 20 (1 1/2-inch) balls. Continue as directed in recipe.

Now that you’ve tried our pineapple upside-down cookies, you may want to try it in cake form, and we’ve got you covered.

Easy Pineapple Upside-Down Cake is a delicious one-layer cake made with Betty Crocker™ Super Moist™ Yellow Cake Mix.

Pineapple Upside-Down Skillet Cake puts a spin on the classic by baking the cake in a 12-inch cast-iron skillet.

Slow-Cooker Pineapple Upside-Down Cake will deliver a delicious cake, no oven necessary.