Chocolate Cherry Thumbprint Cookies

A Christmas confession: I’ve somehow made it this far into the season without baking any cookies at all. Like the rest of this crazy year, these weeks between Thanksgiving and Christmas have just zipped by, and I find myself expecting Christmas guests without ANY cookies in my house!

Since I don’t have time to make a bunch of different ones, I went on a quest to find just one perfect cookie that could be the best festive treat. Luckily, I have my TipHero family on my side, and they were ready with a GREAT idea: these Chocolate Cherry Thumbprint Cookies!

These treats were just made for Christmas, in every way possible, from the delicious chocolate cookie to the sweet and tart cherries chilling in the middle of powdered sugar like ornaments on a snowy tree. Even better, they’re actually pretty simple to make, believe or not. Let us show you how, then read on for the full recipe so you can get in on the last-Christmas-minute baking fun, too!

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Chocolate Cherry Thumbprint Cookies

Makes about 2 dozen cookies
Prep Time: 1 hour
Total Time: 1 hour 15 minutes


  • 1 cup flour
  • ⅓ cup unsweetened cocoa powder
  • ¼ cup brown sugar
  • ¼ cup sugar
  • ¼ teaspoon baking powder
  • ½ teaspoon salt
  • ⅓ cup butter, melted
  • 1 egg, room temperature
  • 2 tablespoons milk
  • 1 teaspoon vanilla extract


  • ½ cup granulated sugar
  • ½ cup powdered sugar
  • 1 cup cherry pie filling


  1. Preheat the oven to 350 degrees Fahrenheit (175 degrees Celsius). Line 3 baking sheets with parchment paper or a silicon baking mat.
  2. In a large mixing bowl, whisk together the flour, unsweetened cocoa powder, ¼ cup brown sugar, ¼ cup sugar, baking powder, and salt until well-combined.
  3. In a separate bowl, whisk together the melted butter, egg, milk and vanilla extract until well-combined.
  4. Add the wet ingredients to the dry ingredients and mix until just combined.
  5. Portion and roll the cookie dough into 1 inch balls, about 1 scant tablespoon each.
  6. Allow the balls of cookie dough to chill in the refrigerator for 30 minutes to 1 hour.
  7. Roll the balls of chilled cookie dough in the ½ cup of granulated sugar and set aside until all the cookie dough balls are sugared.
  8. Roll the sugared cookie dough balls in the ½ cup of powdered sugar, making sure to coat thoroughly, and place on the lined baking sheets.
  9. Using your thumb or the back of a teaspoon, make a “thumbprint” indention in the center of each cookie dough ball to leave room for cherry pie filling. Do not press completely through the cookies. Repeat this process with the remaining dough.
  10. Bake the coated and indented cookies for 10 to 12 minutes.
  11. Remove the cookies from the oven and, if needed, press the centers of the cookies again to redefine the indentations.
  12. While the cookies are still warm, spoon a cherry and a small amount of filling into each of the “thumbprint” indentations.
  13. Remove the cookies from the baking sheets and allow to cool completely on a cooling rack.

Aren’t these Chocolate Cherry Thumbprint Cookies the most festive little treats you’ve ever seen?! We love the way the crinkle of the thumbprint and the powdered sugar topping combine to create the effect of new-fallen snow, and the cherries give them just the right spark of merry Christmas color.

Now that I know what I’ll be finally making for my Christmas cookies, what do YOU think? Will you try to whip some up before the big day? Have you ever made any treats like these ones before? What other kind of “thumbprint” cookies do you enjoy making? Tell us what you think, if you give them a try, and how they turn out for you!