Spiced Chocolate Pudding

Whisk cocoa powder, cornstarch, sugar, salt, espresso powder, and cinnamon until combined in heavy-bottomed medium saucepan. Whisk milk into sugar mixture until smooth. Add chocolate and bring to simmer, whisking occasionally and scraping down sides of saucepan as necessary, over medium heat.

Reduce heat to medium-low and cook, stirring constantly with heatproof rubber spatula and scraping edges and bottom of saucepan until thickened and large bubbles appear at surface, 2 to 4 minutes. (Mixture will become thick and glossy.) Off heat, stir in vanilla.

Immediately pour pudding through fine-mesh strainer and into large bowl, pushing gently with spatula leaving any solids in strainer. Place plastic wrap directly on surface of pudding to prevent skin from forming. Refrigerate for at least 4 hours until set or until completely chilled. (Pudding will keep for up to 2 days.) Gently stir pudding before transferring to individual bowls and serving.