Chocolate Thumbprints with Cherries and Walnuts

Preheat the oven to 350 degrees F (175 degrees C). Line a baking sheet with parchment paper.

Place 1/2 cup chocolate chips and 1 tablespoon shortening in the top of a double boiler over simmering water. Stir frequently, scraping down the sides with a rubber spatula to avoid scorching, until chocolate is melted, about 5 minutes. Set aside to cool.

Combine sugar and butter in a large bowl and beat with an electric mixer on medium speed until fluffy. Beat in cooled chocolate mixture. Add egg, milk, and vanilla extract; beat until well combined. Add flour, cocoa powder, baking powder, espresso powder, and salt; beat on low speed until just combined and a dough forms.

Shape dough into 3 dozen 1-inch balls and roll in chopped walnuts to coat. Place balls 1 inch apart on the prepared baking sheet. Make an indentation in the center of each cookie using your thumb.

Bake in the preheated oven until the edges are firm, 8 to 10 minutes. Transfer cookies to a wire rack and let cool, about 30 minutes.

While cookies are cooling, place remaining 3/4 cup chocolate chips and 1 tablespoon shortening in the top of a double boiler over simmering water. Stir frequently, scraping down the sides with a rubber spatula to avoid scorching, until chocolate is melted, about 5 minutes. Cool slightly.

Spoon a cherry with some of the sauce into the center of each cooled cookie and drizzle chocolate mixture over the tops. Let stand until chocolate is set.