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Pineapple Upside Down Cookies


Try this new version of pineapple upside down cake with these pineapple upside down cookies.

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Rate this recipe 3.6/5 (9 Votes)


  • Icing:
  • 3 cups all purpose flour
  • 1/2 teaspoon baking soda
  • 1/2 teaspoon baking powder
  • 1/4 teaspoon salt
  • 1 stick butter, room temperature
  • 1 cup light brown sugar
  • 2 eggs
  • 1 teaspoon vanilla extract
  • 3/4 cup sour cream
  • 2 (20-ounce) cans crushed pineapple, well drained
  • 1 Stick Butter
  • 1 Cup Light Brown Sugar
  • 1/4 Cup Heavy Cream plus a few extra tablespoons to reach desired consistency(or milk or half and half, use what you have)
  • 1 + 3/4 Cup Confectioner’s Sugar


Servings 2
Preparation time 20mins
Cooking time 92mins
Adapted from


Step 1

Preheat oven to 350°F.

Sift together dry ingredients ( flour, baking soda, baking powder, and salt). Set aside.

In a large mixing bowl, blend together (with hand or stand mixer) butter and brown sugar. Beat in eggs, vanilla, and sour cream. Add the well drained crushed pineapple and mix well. Remember to scrape down sides and bottom of bowl, ensuring even mixing.

With mixer on low, slowly add the dry ingredients and mix until all the flour has been incorporated.

Scoop dough out onto parchment lined cookie sheets about 2 inches apart (they will spread slightly). Bake in preheated oven for about 12 minutes. Remove from oven and transfer to cooling rack. Ice cookies once they are completely cool.


In a small saucepan over medium heat, melt the stick of butter. Once the stick of butter has melted stir in the brown sugar and stir to dissolve. Bring mixture to boil and then reduce heat to medium low and continue to boil for 2 minutes. Once the two minutes are up, stir in the cream and return to boil, stirring constantly. Once it reaches a boil, remove from heat and let cool.

Once the mixture is at least lukewarm, transfer it to a mixing bowl and with beaters on low, slowly add the confectioners sugar and beat to desired consistency. You may want to add extra cream/milk to icing to make it thinner - I did.

Tip: I made my icing the night before and stuck it in the fridge, the next morning it was rock hard! I stuck it in the microwave for one minute to loosen it up, stuck it back in the mixing bowl and slowly added more cream (little by little) until I reached the desired consistency. The thinner the icing the easier it is to ice the cookies.

The icing will thicken/harden the longer it sits, so ice the cookies as soon as the icing is ready to go

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