Ingredients
3/4 cup sugar
1/4 cup cornstarch
1/4 teaspoon kosher salt
2 1/2 cups whole milk
2 tablespoons espresso powder
4 large egg yolks
1 teaspoon pure vanilla extract
1/4 cup mascarpone, plus more for serving
1/2 cup espresso or strong coffee
1/4 cup brandy
18 to 24 amaretto cookies
Dutch-process cocoa powder, for dusting
Chocolate curls, for serving
Preparation
Combine sugar, cornstarch, and salt in a medium saucepan. Whisk in milk and espresso powder; cook over medium-high, stirring constantly, until bubbling and thick, about 2 minutes after it comes to a boil.
In a bowl, whisk yolks until combined. Pour in milk mixture in a slow, steady stream, whisking until completely incorporated. Return mixture to saucepan and cook over medium, stirring constantly, until it returns to a boil, 1 to 2 minutes. Remove mixture from heat and stir in vanilla. Whisk in mascarpone until smooth. Let cool slightly.
Combine espresso and brandy in a shallow bowl. Quickly dip cookies in espresso-brandy mixture. (Cookies should absorb some of liquid but not become mushy.) Place cookies in a snug layer in the bottom of small glasses or Mason jars, 3 or 4 per glass.
Whisk pudding until smooth and divide among glasses, topping cookies. Refrigerate until firm, at least 2 hours and up to overnight.
Dust tops with cocoa and dollop with mascarpone. Sprinkle with chocolate curls; serve.