Rachel Cooks

Chocolate-Cherry Thumbprints

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. I think the traditional jelly 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. They’d be fun to experiment with and add in different flavorings.


Chocolate Cherry Thumbprints

These chocolate cherry thumbprints have a moist, chocolatey cookie base with a smooth cherry filling.


  • 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)


  1. Preheat oven to 350 degrees F. 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.
  2. 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 at 350 degrees. Remove 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.
  3. 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).
  4. 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).

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 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.



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33 Responses to “Chocolate-Cherry Thumbprints”

  1. Jennifer @ Not Your Momma's Cookie — December 10, 2012 at 7:14 am

    These sound totally delicious!

  2. DessertForTwo — December 10, 2012 at 8:12 am

    These are so cute! And what a fun flavor combo!

  3. Colleen @ What's Baking in the Barbershop?! — December 10, 2012 at 8:18 am

    YUM! Chocolate and cherry is such a great combo. These cookies look so perfectly chewy!

  4. Laurie {Simply Scratch} — December 10, 2012 at 8:19 am

    I love thumbprints too… and the whole chocolate-cherry combo… and the sprinkles… and the… 😉

  5. brandi — December 10, 2012 at 8:46 am

    yum, i want these for my coffee break snack! they’re a pretty holiday cookie :)

  6. Abby @ The Frosted Vegan — December 10, 2012 at 8:51 am

    Love those cute little sprinkles and anything with a fudge center is a win in my book!

  7. Kathryn — December 10, 2012 at 8:55 am

    I’m having a total craving for these – I’m going to have to go home and make them one night after work!

  8. kelley {mountain mama cooks} — December 10, 2012 at 9:00 am

    These are adorable! And the possibilities are endless with flavoring!!

  9. sally @ sallys baking addiction — December 10, 2012 at 9:06 am

    Just the other day I was eating a chocolate covered cherry and contemplated making chocolate covered cherry brownies but then I got too lazy. I think you read my mind b/c staring at these beautiful cookies with one of my favorite flavor combinations is making my morning. Rachel, these are so adorable and I can only imagine how inedible they taste – cherry extract next time, that’s a good idea. LOVE the sprinkles!

  10. Lauren @ Climbing Grier Mountain — December 10, 2012 at 9:52 am

    These thumbprints look divine! I’m a big fan of cherry and chocolate. I could use one right now with breakfast!

  11. sarah k @ the pajama chef — December 10, 2012 at 10:48 am

    growing up we always made traditional thumbprints too. these sound yummy!

  12. Mackenzie {SusieFreakingHomemaker} — December 10, 2012 at 11:16 am

    I love thumbprints too! Sadly, I have never made them – these have convinced me that I must do so immediately!!

  13. Katrina @ In Katrina's Kitchen — December 10, 2012 at 11:25 am

    These are adorable! And calorie-free right? :)

  14. Steph — December 10, 2012 at 12:40 pm

    You had me at chocolate! But then the cherry thumbprint part made it even better!

  15. Kim Bee — December 10, 2012 at 1:43 pm

    These are freaking adorable. And being made. Like immediately.

  16. amanda @ fake ginger — December 10, 2012 at 2:06 pm

    Oooh, love these! I don’t think I’ve ever seen cherry thumbprints. I totally need to get my hands on some cherry extract.

  17. natalie@thesweetslife — December 10, 2012 at 2:15 pm

    my grandma makes the same ones with the walnuts and icing! too funny :)

    these sound great–I’m thinking they’d be awesome with a mint filling too!

    • Rachel — December 10th, 2012 @ 2:16 pm

      The original recipe used a mint filling. My mom made them last year and they were amazing! My month was filled with too many mint treats already, though. 😉

  18. Erin @ Dinners, Dishes and Desserts — December 10, 2012 at 2:36 pm

    I had a cookie exchange yesterday that these would have been perfect for!

  19. Rachel @ Baked by Rachel — December 10, 2012 at 4:17 pm

    They look absolutely perfect! I’ve never actually had a chocolate thumbprint before but I want one now. And those red sprinkles are the best addition!

  20. Dana @ Simply Romanesco — December 10, 2012 at 4:46 pm

    These cookies are so cute and festive! And all that chocolate… who could resist them? :)

  21. Jamie @ Thrifty Veggie Mama — December 10, 2012 at 8:52 pm

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

  22. Megan {CountryCleaver} — December 10, 2012 at 9:34 pm

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

  23. Susan — December 11, 2012 at 4:51 pm

    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.

    • Rachel — December 11th, 2012 @ 9:29 pm

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

  24. Mom — December 11, 2012 at 7:06 pm

    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 :)

  25. Cathy @ Noble Pig — December 11, 2012 at 7:38 pm

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

  26. Kimberly — November 23, 2013 at 7:25 am

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

    • Rachel Gurk — November 24th, 2013 @ 1:36 pm

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


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