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Cherry Chocolate Thumbprint cookies on counter with bowl of cherry filling and spilled chocolate chips

Chocolate Thumbprint Cookie with Filling

These thumbprint cookies are simple, decadent and irresistibly festive with their red cherry centers!
Course Christmas Cookies, Cookies, Dessert
Cuisine American, English
Keyword Chocolate Thumbprint Cookies, Filled Cookies, Thumbprint Cookies
Prep Time 10 minutes
Cook Time 10 minutes
Filling 10 minutes
Total Time 30 minutes
Servings 3 Dozen
Author Melissa


  • Stand (or electric) mixer
  • Saucepan


  • ½ cup Semi-Sweet Chocolate Chips
  • 2 tbsp Shortening
  • ½ cup Butter - unsalted
  • ¾ cup Sugar
  • 1 Egg
  • 1 tbsp Milk we used 1%
  • 1 tsp Vanilla Extract
  • 2 cups Flour
  • 2 tbsp Cocoa Powder
  • 1 tsp Baking Powder
  • ¼ tsp Salt
  • ½ cup Finely Chopped Roasted Almonds
  • 1 can Cherry Pie Filling (with whole cherries)


  • Preheat oven to 350 °F and line baking sheet with parchment paper.
  • Add ½ cup of semi sweet chocolate chips along with the shortening to a small saucepan. Melt over low heat- stirring frequently. Remove from heat and allow to cool while you prepare the dough.
  • In stand mixer cream together butter and sugar on medium speed until fluffy. Add in cooled chocolate and beat to combine.
  • Add egg, milk and vanilla - beat on medium speed to fully combine.
  • In a medium bowl sift or whisk together your dry ingredients (flour, cocoa powder, baking powder and salt). Add to wet mixture and beat on low speed to just combine.
  • Shape dough into 1" balls and roll in chopped almonds. Place the balls approximately 1" apart on your prepared baking sheet and gently make an indentation in the center of each ball using your thumb.
  • Bake for 10-12 minutes, or until the edges are firm. Transfer to wire cooling rack and cool completely. You may need to use the back of a wooden spoon to gently press your indent again once they are removed from the oven.
  • Using a small spoon gently place a cherry in each indent - we added a small amount of pie filling as well to give it more texture while eating!