Chocolate Thumbprint Cookies, perfect for the holidays!

Chocolate Thumbprint Cookies for Hanukkah and Christmas!

Last week, we hosted a Hanukkah Dinner Party. One of the cookies I made for this dinner was these Chocolate Thumbprint Cookies, which I found on a Jewish website about foods for Hanukkah.

I think I already posted, we are not Jews, but my husband and I did a several year Hebrew study and learned a lot about the different Jewish holidays an dfeasts. As Christians, we celebrate Christmas. But, there are quite a few Jewish holidays that are fun to celebrate and have a message that points to Jesus, as does Hanukkah. Since my daughter-in-law, Jennifer, had already told me that one of her favorite Christmas cookies were Thumbprint Cookies, I decided to give these a try. Typically, we think of Thumbprint Cookies with Cherry or Apricot filling, so these Chocolate Thumbprint Cookies are a different twist on that theme. (Once again the music side of me coming out!)

Making the Chocolate Thumbprint Cookies . . .

Since I had never made thumbprint cookies of any kind, making these Chocolate Thumbprint Cookies was a new adventure for me. The process was easy, and the cookies really good . . . almost like a chocolate shortbread cookie rolled in powdered sugar. To me, the hardest part of making the cookies was trying to chop the chocolate chips! I tried with a nut chopper. That didn’t work. I then put the chips in my food processor. That ground some to powder, others were still a little large. You can see in the picture below that there are some nice-sized pieces of chocolate chips in the cookie dough.

Having never made Thumbprint cookies before, I wasn’t sure about how deep to press into the cookie dough to create the indentation that would hold the chocolate filling. I pressed about 1/2-3/4 of the way into the cookie dough. I still had to use the end of a rounded spoon handle before taking out of the oven to press the indentation down, because I thought there wasn’t enough of a “hole” to hold the filling.

Once out of the oven, the indented thumbprint cookies are rolled in powdered sugar and set aside to cool while the filling is made. I did re-roll some of the cookies if I thought there wasn’t enough powdered sugar on them.

The last step is to pipe the filling into the indentations in the cookies. I added a little powdered sugar to the filling to give it a bit of substance. That may have been an unnecessary step.

The cookies were a lovely addition to our Dessert Table, and quite tasty to eat. Over all, this is a really good variation of a Thumbprint Cookie, especially if you like chocolate.

What is your favorite Thumbprint Cookie?

Chocolate Thumbprint Cookies

Chocolate Thumbprint Cookies Recipe

These lovely Chocolate Thumbprint Cookies are a variation of the fruit-filled ones we associate with the holidays. They are like a chocolate shortbread cookie, rolled in powdered sugar, and filled with a luscious chocolate filling.






Ingredients for Cookies:

  • 3
  • 1
  • 1
    brown sugar
  • 3
  • 1/4
  • 1
    chocolate chips, divided

Ingredients for Filling:

  • 2
  • 1/4
    light corn syrup
  • 2
  • powdered sugar


Instruction for Cookies:

  1. Chop 1/4 of the chocolate chips. (I tried a nut chopper and my food processor to chop the chips. I did not try just cutting with a knife on a cutting board because of them rolling off.)

  2. In a mixing bowl, combine butter, brown sugar, and 3 teaspoons vanilla. 

  3. Add flour, milk, and chopped chips. Shape in 1/2-inch balls. 

  4. Place cookie dough balls on ungreased cookie sheet, and make a depression, or indentation, in center of each cookie with your thumb. 

  5. Bake 10 to 12 minutes at 375° . Remove from oven, and then roll in powdered sugar. Place on wire racks to cool while making filling.

Instruction for Filling:

  1. In a small bowl over hot water, combine the rest of the chips and the shortening. Stir until melted. Remove from heat.

  2. Add corn syrup, 2 tablespoons water, and the 2 teaspoons vanilla. Stir to combine. Fill each cookie.

  3. Makes about 4 dozen.

Recipe Notes

NOTE: I added a little powdered sugar to the filling because I thought it was too thin. You decide if you want the filling to be thin or have some substace.



I’m a writer, new mom and foodie. I love sharing what I know while making others feel beautiful. On this blog, I share my healthy lifestyle, simple meals, fitness tips and experiences.

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Kara Bout It