Chocolate Cherry Thumbprint Cookies

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

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.

Need more cookie recipes?

I don’t blame you! Try these:

 

• Easy Red Velvet Cookies
• Peppermint Sugar Cookie Sandwiches with Chocolate Ganache Filling
• Peppermint Chocolate Sugar Cookies
• Gingerbread Shortbread Cookies with Cranberries
• Dark Chocolate and Pecan Cookies

 

Continue to Content

Chocolate Cherry Thumbprint Cookies

Prep Time: 15 minutes

Cook Time: 9 minutes

Total Time: 24 minutes

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 (2 1/2 sticks) unsalted butter, softened
• 1 1/2 cups sugar, divided
• 1 large egg
• 1 tablespoon pure vanilla extract
• 4 ounces (3/4 cup) semisweet chocolate chips
• 1 1/2 teaspoons pure cherry extract
• red sprinkles (optional)

Instructions

1. Preheat oven to 350°F. Prepare baking sheet by lining with parchment paper.
2. 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.
3. 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.
4. 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.
5. 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).
6. 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 Information:

Yield: 36 Serving Size: 1 cookie
Amount Per Serving: Calories: 90Total Fat: 2gSaturated Fat: 1gTrans Fat: 0gUnsaturated Fat: 1gCholesterol: 6mgSodium: 21mgCarbohydrates: 17gFiber: 1gSugar: 11gProtein: 1g

RachelCooks.com sometimes provides nutritional information, but these figures should be considered estimates, as they are not calculated by a registered dietitian. Please consult a medical professional for any specific nutrition, diet, or allergy advice.

Did you make this recipe?

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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.