01 - In a medium saucepan, whisk together granulated sugar, unsweetened cocoa powder, cornstarch, and salt until well blended.
02 - Gradually whisk in the whole milk to the dry mixture, ensuring the consistency is smooth and free of lumps.
03 - Place the saucepan over medium heat. Cook, whisking constantly, until the mixture begins to thicken and reaches a gentle boil, approximately 5–7 minutes.
04 - Remove the saucepan from the heat. Stir in the vanilla extract and semi-sweet chocolate chips until the mixture is smooth and the chocolate is fully melted.
05 - Pour the pudding into individual serving dishes. Cover the surface of each dish directly with plastic wrap to prevent a skin from forming.
06 - Refrigerate the pudding for at least 2 hours, or until completely set.
07 - While the pudding chills, beat the cold heavy whipping cream, powdered sugar, and vanilla extract in a cold mixing bowl using a hand mixer or whisk until soft peaks form.
08 - Once the pudding is set, top each serving with a generous dollop of the prepared whipped cream and serve immediately.