Chocolate Thumbprint Shortbread Cookies
Cookies,  Desserts

Chocolate Thumbprint Shortbread Cookies

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Chocolate thumbprint cookies with a melt in your mouth chocolate and a shortbread cookie crust.

I had wanted to recreate a chocolate thumbprint shortbread cookie we used to eat as kids. They actually had a Hershey Kiss in the center. I thought I was purchasing Kisses when I bought Ghirardelli’s Thumbprint Drops, not realizing they’re a flat version and more like a wafer.

They were still good! Like melt in your mouth, gooey good.

I still prefer the Hershey Kisses and their cool chocolate bite, but the choice is yours on which to use. I included them both on the recipe card!

Chocolate Thumbprint Shortbread Cookie


Chocolate Thumbprint Shortbread Cookies

Recipe by Simply Happenings


Prep Time


Cooking Time



Chocolate thumbprint cookies with a melt in your mouth chocolate and a shortbread cookie crust.


  • 1 cup All-Purpose Flour

  • 1 cup Confectioners’ Sugar

  • 1/2 cup Cold Butter

  • 1 tsp Vanilla Extract

  • 48 Milk Chocolate Hershey Kisses or Ghirardelli Baking Milk Chocolate Thumbprint Drops


  • Preheat oven to 350 degrees Fahrenheit. Spray cookie sheet with cooking spray or line cookie sheet with parchment paper.
  • Mix flour, confectioners’ sugar, vanilla extract, and cold butter together in mixer or with hand mixer. At first it will crumble and look dry, but keep mixing and it will form into a ball.
  • Roll dough into 1″ balls and place them 2″ apart on cookie sheet.
  • Bake for 12-15 minutes until bottom of cookies are golden brown. Remove pan from the oven and press a chocolate drop or kiss on cookie while cookie is still hot. Allow to cool on cooling racks.


  • Angie

    I was confused by the recipe as I followed instructions exactly and the dough would not come together. Overbeating the dough lead to these coming out rock hard! It seems there is not enough liquid in the batter but please let me know if I’m missing something

    • Tiffany

      Hello Angie. I’m sorry the dough did not turn out for you!
      At first, the dough is rather dry and flaky, but as the half cup of butter warms it will moisten the dough, but the dough should not stick to the sides of the bowl. It should be a somewhat firm cookie dough that can be used to form balls or like a cookie-cutter dough.
      Also, I should have specified to use all-purpose flour (any baker’s terrible mistake!) and have updated the recipe to reflect this. I am wondering if that is the cause of the hard dough if you used a different type because that can lead to very different results.
      – Tiffany

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