Pineapple Upside Down Cookies

This is another recipe that is definitely not low carb, but I’ve had a few people request the recipe. These are insanely easy to throw together and are great for big groups of people. Enjoy!

Pineapple Upside Down Cookies

Servings: 3 Dozen Prep Time: 10 minutes (plus 1 hour chilling time) Bake Time: 8 minutes Total Time: 1 hour, 18 minutes



  1. In a mixing bowl, attached to a stand mixer or using a hand mixer, mix the Pineapple Supreme Cake Mix, eggs, and canola oil on medium speed until well combined.
  2. Cover the bowl with saran wrap and refrigerate the dough for one hour or up to one day.
  3. While dough is chilling, begin cutting maraschino cherries in half. Place each half, pit side down, on a paper towel to dry.
  4. Pre-heat oven to 350 degrees F. Line four cookie sheets with parchment paper or silicone baking mats. Set aside.
  5. Remove dough from refrigerator. Spoon out dough, approximately 1 tbsp. size, and roll into a ball. Place each ball about 2 inches apart from each other on prepared baking sheet.
  6. Using the flat side of a spoon, make an indention into each cookie, about 1/4 inch deep.
  7. Place one half of a cherry on each cookie. Lightly sprinkle powdered sugar over each cookie.
  8. Bake each tray of cookies for 8 minutes. Cookies will rise and then fall slightly. This is normal.
  9. Let cookies cool on baking tray for five minutes. Remove cookies from tray and allow to cool completely on a wire baking rack.

Cookies stored in an airtight container are good for up to 10 days.

Make ahead instructions: To freeze, roll dough into balls. wrap tightly in saran wrap, and then in aluminum foil. Place in a ziploc freezer bag. Frozen cookie dough is good for up to two months. When ready, thaw dough in the refrigerator overnight and begin at step 5.