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Chocolate Cherry Cookies

Chocolate cherry cookies pair soft cocoa cookies with a maraschino cherry and a smooth chocolate topping. Bake until the edges are set, then spoon on the warm topping for a glossy finish.
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Prep Time 20 minutes
Cook Time 12 minutes
cooling time 5 minutes
Total Time 37 minutes
Servings: 24 servings
Course: Dessert
Cuisine: American
Calories: 162
Ingredients Equipment Method Notes

Ingredients
  

For the cookie dough
  • 0.5 cup unsalted butter softened
  • 1 cup granulated sugar
  • 1 egg large
  • 1 tsp vanilla extract
  • 1.5 cup all-purpose flour
  • 0.5 cup unsweetened cocoa powder
  • 0.5 tsp baking soda
  • 0.25 tsp salt
  • 0.25 cup milk
For the cherry-chocolate topping
  • 24 maraschino cherries drained and patted dry
  • 1 tbsp maraschino cherry juice from the jar; reserved
  • 1 cup semisweet chocolate chips
  • 0.5 cup sweetened condensed milk

Equipment

  • 2 large baking sheets
  • 1 electric mixer
  • 1 microwave

Method
 

Prepare the cookie dough
  1. Heat the oven to 350°F.
  2. Line two large baking sheets with parchment paper.
  3. In a large bowl, beat the butter and sugar until pale and fluffy, about 2 minutes.
  4. Beat in the egg and vanilla until combined.
  5. In a medium bowl, whisk together the flour, cocoa powder, baking soda, and salt.
  6. Add the flour mixture to the butter mixture in three additions, alternating with the milk in two additions and beginning and ending with the flour mixture; mix just until combined.
Bake and fill the cookies
  1. Scoop the dough into 24 portions, about 1 1/2 tablespoons each.
  2. Arrange 12 portions on each baking sheet, spacing them about 2 inches apart.
  3. Bake both sheets for 10–12 minutes, switching and rotating their positions halfway through, until the edges are set.
  4. Immediately press a shallow indentation into each cookie with the back of a teaspoon.
  5. Place a cherry in each indentation.
  6. Let the cookies cool on the baking sheets for 5 minutes.
  7. Transfer the cookies to a wire rack and cool completely.
Make the chocolate topping
  1. Combine the chocolate chips and sweetened condensed milk in a microwave-safe bowl.
  2. Microwave at 50% power in 20-second intervals, stirring each time, until smooth.
  3. Stir in the reserved cherry juice.
  4. Spoon about 1 tablespoon of the chocolate mixture over each cherry.
  5. Let the topping set before serving.

Notes

Pat the cherries thoroughly dry so the chocolate topping settles neatly. Store in an airtight container in the refrigerator for up to 5 days; freezer: yes. For a dairy-free swap, use dairy-free butter, milk, chocolate chips, and sweetened condensed milk.