Preparation Steps

• Place the chopped chocolate in a medium heatproof bowl. Sprinkle the espresso powder over it and add the vanilla extract; set aside.
• Pour the Cabernet into a small saucepan and bring to a gentle simmer over medium heat. Cook until reduced by about half (to roughly 1/3 cup), 5–7 minutes. Take off the heat and keep warm.
• In a separate medium saucepan off the heat, whisk together the sugar, cornstarch, and salt. Slowly add the cold milk, whisking until perfectly smooth with no lumps.
• Whisk the warm reduced wine into the milk mixture. Set the pan over medium-low heat and cook, whisking constantly and scraping the corners, until the pudding thickens and slow bubbles break the surface, 5–7 minutes.
• Once you see steady, lazy bubbles, continue to cook for 60–75 seconds to fully activate the cornstarch. Remove from heat.
• Immediately pour the hot pudding base over the chocolate mixture. Let it sit for 1 minute, then whisk until the chocolate is completely melted and the pudding is glossy and smooth.
• Strain through a fine-mesh sieve into a clean bowl or spouted measuring cup to ensure a perfectly silky texture.
• Divide into 4 small cups. Press plastic wrap directly onto the surface of each to prevent a skin. Cool at room temperature for 30 minutes, then refrigerate 1 1/2–2 hours, until softly set and chilled.
• Serve as-is or top with a spoonful of lightly sweetened whipped cream and a few fresh berries, if you like.