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Dark Chocolate Cherry Thumbprints

  • Prep 15 min
  • Total 1 hr 15 min
  • Servings 30
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With a powdered sugar coating and a yummy chocolate filling, these cookies are always a cookie-plate fave! MORE + LESS -

Susan Denney
April 27, 2015


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)


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
It's cookie week at Tablespoon, just in time for holiday baking! Check out all channels during the coming week as we dive into dough to bring you the best of the best!

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.

So, here we go!

First, make a quick dough. I use a stand mixer to get the dough to this crumbly but stick-together stage:

If you have a 1-1/4" cookie scoop, a rounded heap will plop out just the right amount of crumbly dough into your palm. (If you don't have a scoop, eyeball it with a large spoon.)

Roll the dough between the palms of your hands to make a 1" ball, then let your thumb have some fun.

You want to make a good size indent so you have plenty of space to fill with melted chocolate later. Then they're ready for the oven:

Bake at 375 degrees for about 10-12 minutes. They should be set but not hard or brown when done. Remove from the cookie sheet to a cooling rack and let 'em cool.

When they're all cooled down, give 'em a dunk in a powdered-sugar bath.

I put a sheet of wax paper underneath to make clean-up a breeze.

Now the yummy part. Put the chocolate ingredients into a microwave-safe bowl.

Micro for 20 seconds, stir, and micro again for another 5-10 seconds. Stir like crazy until the ingredients are all silky smooth.

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.

When you've filled the cookies, let the chocolate set up a bit.

You could stop right here 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:

Peppermint Whoopie Pies Recipe
Chocolate Peppermint Biscotti Recipe
Holiday Star Cookies Recipe
Holiday Cookie Ornaments Recipe
Easy Gingerbread Friends Recipe

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