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Dark Chocolate Cherry Thumbprints

  • Prep 15 min
  • Total 1 hr 15 min
  • Servings 30

With a powdered sugar coating and a yummy chocolate filling, these cookies are always a cookie-plate fave! MORE + LESS -

TBSP Susan
May 10, 2017


cup butter, softened but not melted
cup brown sugar
teaspoon salt
teaspoon vanilla
to 2 tablespoon milk (so mixture can be easily rolled into balls)
to 1/2 cups Gold Medal™ flour
sugar powdered (to coat cooled cookies)

Filling: Chocolate

cup DARK chocolate chips
tablespoon shortening
tablespoons light corn syrup
tablespoon water
teaspoon cherry juice (from Maraschino cherry jar)
maraschino cherries (stems removed and well drained)


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  • 1
    In a stand mixer, cream softened butter with the brown sugar. Add salt, vanilla and 1 tbsp milk, and mix until well blended. Add flour and mix until mixture forms coarse crumbs that stick together. (Add additional 1 tbsp milk if needed.)
  • 2
    Using a spoon or a 1-1/4 inch cookie scoop, put dough into palm of hand and roll between palms to form a 1 inch to 1-1/4 inch ball. Place balls on ungreased cookie sheet.
  • 3
    With thumb, form deep indent in each cookie. Bake at 375° F for 10-12 minutes until firm but not brown. Remove cookies from sheet to a cooling rack and cool completely.
  • 4
    When cookies are cool, roll them in powdered sugar to coat thoroughly.
  • 5
    Add filling ingredients (dark chocolate chips, shortening, corn syrup, water, and cherry juice -- NOT maraschino cherries) to a microwave-safe dish. Micro on high for 20 seconds. Stir and micro again another 10 seconds. Mix chocolate until silky smooth. Return to micro 5 seconds at a time if necessary.
  • 6
    Using a pastry bag or small spoon, fill each cookie indent with a mound of melted chocolate. Allow chocolate to set a few minutes, then add well-drained maraschino cherry to top of each cookie. Serve immediately or refrigerate no more than 2 hours.

Expert Tips

  • Make cookies and freeze or store in air-tight container until needed. Mix chocolate filling just before serving. Top with cherry and serve.

Nutrition Information

No nutrition information available for this recipe
More About This Recipe
  • When I was growing up, there were a couple classic Christmas cookies that were absolutely non-negotiable at holiday time: sugar cookie cut-outs and thumbprints with chocolate filling. I've taken my mom's classic thumbprint recipe (from who knows how long ago) and updated it for today's sophisticated cookie connoisseurs. The diff? Silky, sinfully rich dark chocolate replaces the semi-sweet filling, and a rosy, shiny maraschino cherry crowns the top, making sure these Dark Chocolate Cherry Thumbprints will be the belles of the cookie-plate ball. When it's time to add the chocolate, you can pipe the chocolate into the thumbprint indents using a pastry bag (or a Ziploc bag with the corner clipped off), but I like using a baby spoon. It's just the right size. You could stop right here with just the chocolate and be in cookie heaven. But add some Christmas red with well-drained maraschino cherries, and you take these holiday goodies right over the top. These cookies could bring peace on earth and joy to the world -- they're that yum. GO! Make these now! Classic Christmas Cookies For more cookie-plate ideas, try these cookie recipes!

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