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Chocolate Covered Cherry Cookies on a white plate with maraschino cherries.
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3.75 from 93 votes

Chocolate Covered Cherry Cookies

If you are a fan of chocolate and cherries you’ve got to try these Chocolate Covered Cherry Cookies. These fudgy, brownie-like thumbprint cookies have a sweet cherry peeking through a drizzle of cherry-infused chocolate frosting.
Prep Time25 mins
Cook Time10 mins
Total Time35 mins
Course: Dessert
Cuisine: American
Servings: 24 cookies
Calories: 175kcal


For the Chocolate Thumbprint Cookies

  • ½ cup butter softened
  • ½ cup light brown sugar
  • ½ cup granulated white sugar
  • 1 egg
  • 1 ½ teaspoons pure vanilla extract
  • 1 ½ cups all-purpose flour
  • ½ cup unsweetened cocoa powder
  • ¼ teaspoon salt
  • ¼ teaspoon baking powder
  • ¼ teaspoon baking soda
  • 24 maraschino cherries blotted dry

For the Chocolate Cherry Frosting

  • 1 cup semisweet chocolate chips
  • ½ cup sweetened condensed milk
  • 2 tablespoons reserved maraschino cherry juice plus additional as needed


  • Preheat oven to 350 degrees F.
  • In a large mixing bowl, use an electric mixer to cream together the butter and sugars until fluffy. Beat in the egg and vanilla.
  • In a separate bowl combine the dry ingredients and then add to creamed mixture a little at a time, beating until well combined.
  • Using a small cookie scoop and/or your hands, shape the dough into 24 balls, about 1-inch round, and place them on ungreased or parchment paper lined baking sheets. Slightly indent each ball of dough with one of your fingers and then place one maraschino cherry in each indentation.
  • Bake for 10 to 11 minutes. Remove from the oven and allow cookies to cool on the baking sheets for about 5 minutes. Transfer cookies to wire racks to cool completely.

Easy Chocolate Cherry Frosting

  • Meanwhile, melt chocolate chips and sweetened condensed milk in a small, heavy saucepan over LOW heat, stirring constantly. Remove from the heat, add 2 tablespoons reserved cherry juice, and stir until smooth. Add additional cherry juice, if necessary, to reach the desired consistency.
  • Drizzle the frosting over the cooled cookies or alternately, transfer the frosting to a pastry bag fitted with a small circle tip and pipe over the cookies for a more uniform look.



I like to store frosted cookies in a single layer in a baking pan with a lid to be sure the frosting stays intact. You can also store the cookies in an air tight container between layers of wax or parchment paper after the frosting has had time to set. Store at room temperature and consume within 3 to 4 days.
Freezer Instructions
For the best quality, I recommend freezing unbaked cookies. Once you form the balls of dough, place them on a baking sheet lined with wax or parchment paper and freeze until firm. Transfer them to a freezer bag or other airtight container and freeze for up to 3 months. When ready to bake, thaw the dough completely in the refrigerator. Once thawed, form the indentations, fill with cherries, and bake and frost as directed in the recipe.


Serving: 1cookie | Calories: 175kcal | Carbohydrates: 25g | Protein: 2g | Fat: 8g | Saturated Fat: 5g | Polyunsaturated Fat: 1g | Monounsaturated Fat: 2g | Trans Fat: 1g | Cholesterol: 20mg | Sodium: 83mg | Potassium: 117mg | Fiber: 2g | Sugar: 17g | Vitamin A: 151IU | Vitamin C: 1mg | Calcium: 37mg | Iron: 1mg