These chocolate cherry thumbprint cookies have a moist, chocolatey cookie base with a smooth cherry flavored filling.

These chocolate cherry thumbprint cookies have a moist, chocolatey cookie base with a smooth cherry filling. Get the recipe that's perfect for Christmas on RachelCooks.com!
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Aren’t these cookies the cutest? I love thumbprint cookies of all kinds and have very fond memories of my grandma making them every Christmas. Hers were rolled in chopped walnuts and had a powdered sugar based icing in the thumbprint. She may have used the more traditional jelly filling sometimes, too…if my memory serves me. I’m sure my mom will pipe up in the comments here correcting me if I’m wrong. (Thanks Mom!)

I would highly recommend making these cookies or some version of them. The cookie portion of them is so delicious. The dough is moist, and so full of chocolate flavor.

Make it your own

  • Experiment with the filling and add different flavorings to the chocolate, such as raspberry, orange, almond, maple, amaretto…. Or maybe you like the traditional jam/jelly filling or a frosting made with powdered sugar. 
  • I rolled these in sugar because my family has nut allergies, but if you like, you could roll yours in finely chopped walnuts or pecans.
These chocolate cherry thumbprint cookies have a moist, chocolatey cookie base with a smooth cherry filling. Get the recipe that's perfect for Christmas on RachelCooks.com!
Recipe

Chocolate Cherry Thumbprint Cookies

5 from 1 vote
Prep: 15 minutes
Cook: 9 minutes
Total: 24 minutes
Servings: 24 cookies
These chocolate cherry thumbprint cookies have a moist, chocolatey cookie base with a smooth cherry flavored filling.
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Ingredients 

  • 2 cups all-purpose flour
  • 1/3 cup unsweetened cocoa powder
  • 1/4 teaspoon fine salt
  • 1 1/4 cups unsalted butter, softened (2 ½ sticks)
  • 1 1/2 cups sugar, divided
  • 1 large egg
  • 1 tablespoon pure vanilla extract
  • 4 ounces semisweet chocolate chips (¾ cup)
  • 1 1/2 teaspoons pure cherry extract
  • red sprinkles (optional)

Instructions 

  • Preheat oven to 350°F. Prepare baking sheet by lining with parchment paper.
  • In a medium bowl, whisk together flour, cocoa powder and salt. Using an electric mixer and a large bowl (or a stand mixer), beat 1 cup of butter and 1 cup of sugar on medium-high until light and fluffy (about 3 minutes). Add egg and vanilla and beat until combined. Turn mixer to low and gradually add flour mixture until combined.
  • Put the remaining 1/2 cup of sugar in a small bowl. Roll dough into approximately 1-inch balls and then toss in sugar to coat. Place one inch apart on parchment-paper lined baking sheets.
  • Bake for five minutes. Remove cookies from the oven and use the back of a small round measuring spoon (or a melon baller) to make an indentation in each cookie. Return to oven and bake for another 4 minutes. Cookies should be set but still look moist. Cool on the cookie sheets on wire racks.
  • While cookies cool, microwave chocolate chips and 1/4 cup of butter in a small bowl in 15 second increments. Stir well between each 15 seconds in the microwave, until completely melted. Stir in cherry extract. Let cool slightly so it thickens and you can pipe it without it running out and being a huge mess (about 5 minutes).
  • Spoon mixture into a zip-top bag or a disposable piping bag. Snip a small hole in one corner of the sip-top bag or the end of the piping bag. Pipe chocolate into indentations in cookies and finish with sprinkles (optional).

Nutrition

Serving: 1cookie, Calories: 90kcal, Carbohydrates: 17g, Protein: 1g, Fat: 2g, Saturated Fat: 1g, Polyunsaturated Fat: 1g, Cholesterol: 6mg, Sodium: 21mg, Fiber: 1g, Sugar: 11g

Nutrition information is automatically calculated, so should only be used as an approximation.

Did You Make This?Share a comment and rating below! I love hearing what you think!
These chocolate cherry thumbprint cookies have a moist, chocolatey cookie base with a smooth cherry filling. Get the recipe that's perfect for Christmas on RachelCooks.com!

Verdict: These are so good. The cookie is so rich and decadent and then the filling is smooth and delicious with just the slightest hint of cherry.
Husband’s take: He liked these a lot, too. Took them to work to share with coworkers and to get them out of the house!
Changes I would make: The cherry flavor is very mild, so if you want a stronger taste of cherry, I’d recommend swapping out the vanilla extract in the cookie dough for cherry extract. Should do the trick!
Difficulty: Easy.

These chocolate cherry thumbprint cookies have a moist, chocolatey cookie base with a smooth cherry filling. Get the recipe that's perfect for Christmas on RachelCooks.com!
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29 Comments

  1. Kimberly says:

    I was just wondering how many this recipe yields. I need to do 4 dozen. Thanks so much.

    1. Rachel Gurk says:

      Depending on the size of your cookies — this will probably only yield about 2-3 dozen.

  2. Cathy @ Noble Pig says:

    These are so cute, smple and festive! And my two fave flavors!!

  3. Mom says:

    You’re right–G’ma used to make them filled with powdered sugar frosting, sometimes with colored sugar sprinkled on. She makes similar cookie with almond flavoring and raspberry jam filling, drizzled with a glaze. I’m going to make a citrus thumbprint this year with lemon and lime zest and filled with either lemon curd or orange marmalade. I’m considering making chocolate walnut thumbprints filled with cherry preserves. Maybe I’ll reconsider and make your yummy looking cookies instead :)

  4. Susan says:

    We use the “juice” from the marchino cherry’s in the dough and the chocolate filling. put it in the cookies before baking, top with 1/2 a marchino cherry and sprinkles then bake. I’ve had chocolate cherry thump prints my whole life and never seen/heard another family having them it was so nice to see a similar recipe here.

    1. Rachel says:

      That sounds fantastic! Love adding the cherry on–yum!

  5. Megan {CountryCleaver} says:

    Thumbprints just scream Christmas and cherry during winter just screams holidays! Love these.

  6. Jamie @ Thrifty Veggie Mama says:

    Love these! They look so delicious. I love chocolate cherry combos.