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+ servings
Close-up of rich chocolate cookies with melted chocolate and maraschino cherries.

Chocolate Cherry Thumbprint Cookies

Prep Time 15 minutes
Cook Time 10 minutes
Rich, fudgy, and beautifully topped with glossy chocolate and maraschino cherries, these Chocolate Cherry Thumbprint Cookies are a timeless treat perfect for the holidays or any special occasion.
24 Servings

Ingredients

For the Cookies:

  • 1 cup 2 sticks unsalted butter at room temperature
  • 2 cups granulated sugar
  • 2 large eggs
  • 2 teaspoons pure vanilla extract
  • 3 cups all-purpose flour
  • 1 cup unsweetened cocoa powder
  • 1/2 teaspoon salt
  • 1/2 teaspoon baking soda
  • 1/2 teaspoon baking powder

For the Ganache Filling:

  • 3/4 cup dark chocolate chips
  • 1/4 cup heavy whipping cream
  • 1 tablespoon unsalted butter

For Garnish:

  • 24 maraschino cherries drained and patted dry

Instructions
 

Prepare the oven and baking sheets:

  1. Preheat the oven to 350°F (175°C). Grease or line baking sheets with parchment paper to prevent sticking and ensure even baking.

Cream the butter and sugar:

  1. In a large mixing bowl, combine the butter and granulated sugar. Using an electric mixer, beat on medium speed until the mixture is light and fluffy, approximately 2–3 minutes.

Incorporate the wet ingredients:

  1. Add the eggs one at a time, mixing thoroughly after each addition. Blend in the vanilla extract until fully incorporated.

Combine the dry ingredients:

  1. In a separate bowl, whisk together the flour, cocoa powder, salt, baking soda, and baking powder. Gradually add the dry ingredients to the creamed mixture, stirring just until a soft dough forms.

Shape the cookies:

  1. Roll the dough into 1½-inch balls and arrange them about 1 inch apart on the prepared baking sheets. Bake for 10–12 minutes, or until the edges are set and the centers remain soft.

Create the thumbprint indentations:

  1. Remove the cookies from the oven and, while still warm, use the back of a rounded teaspoon to create an indentation in the center of each cookie. Allow the cookies to cool on the baking sheet for 1–2 minutes, then transfer them to a wire rack to cool completely.

Prepare the ganache:

  1. In a microwave-safe bowl, combine the dark chocolate chips, heavy cream, and butter. Heat in 30-second intervals, stirring between each, until the mixture is smooth and glossy.

Fill and garnish:

  1. Spoon approximately one teaspoon of the ganache into each cookie’s indentation. Top with a maraschino cherry, pressing gently to adhere.

Set and serve:

  1. Allow the cookies to rest at room temperature until the ganache has set, about 30 minutes. Serve and enjoy.

Notes

To make these Chocolate Cherry Thumbprint Cookies gluten-free, substitute the all-purpose flour with a high-quality 1:1 gluten-free baking blend that contains xanthan gum. If the dough appears slightly softer than usual, refrigerate it for 20–30 minutes before shaping to help maintain structure during baking.
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